1-(Thiophen-2-yl)propan-2-one [1-(2-Thienyl)acetone] [C7H8OS]

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21 reactions in Reaxys

2018-06-17 19h:46m:34s (UTC)

S O

1. Query

Search as: Product, As drawn, No mixtures )))

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S

S

O

OH

Rx-ID: 1635768 View in Reaxys 1/21 Yield

Conditions & References

41 %

With chromium(VI) oxide, sulfuric acid in water, acetone, Time= 1h, T= -20 °C Kumamoto, Takanobu; Hosoya, Kumiko; Kanzaki, Satoshi; Masuko, Kazuhiro; Watanabe, Mikio; Shirai, Kozo; Bulletin of the Chemical Society of Japan; vol. 59; nb. 10; (1986); p. 3097 - 3102 View in Reaxys With 2-iodoxybenzoic acid in dimethyl sulfoxide, Time= 2h, T= 0 - 20 °C Li, Jun-Long; Yue, Cai-Zhen; Chen, Peng-Qiao; Xiao, You-Cai; Chen, Ying-Chun; Angewandte Chemie - International Edition; vol. 53; nb. 21; (2014); p. 5449 - 5452; Angew. Chem.; vol. 126; nb. 21; (2014); p. 5553 - 5556,4 View in Reaxys

58 %Spectr. With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, triethylamine in acetone, T= 150 °C , Flow reactor Labes, Ricardo; Battilocchio, Claudio; Mateos, Carlos; Cumming, Graham R.; De Frutos, Oscar; Rincón, Juan A.; Binder, Kellie; Ley, Steven V.; Organic Process Research and Development; vol. 21; nb. 9; (2017); p. 1419 - 1422 View in Reaxys General procedure: The obtained alcohol was dissolved in DMSO and IBX (1.5 equiv) was added at 0 °C. The reactionwas allowed to warm to room temperature and stirred for about 2 h. After completion, the reactionwas quenched with water and extracted with ethyl acetate. The combined organic layers werewashed with brine and dried over MgSO4, filtered and concentrated. The desired ketones wereobtained as a colorless oil after purification by flash chromatography. With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide, T= 0 - 20 °C Zhang, Xiao-Ru; Zhou, Su-Lan; Yuan, Yi; Du, Wei; Chen, Ying-Chun; Synlett; vol. 28; nb. 14; (2017); p. 1771 - 1774 View in Reaxys S O NH S

Rx-ID: 45462027 View in Reaxys 2/21 Yield

Conditions & References With water El-Atawy, Mohamed A.; Ferretti, Francesco; Ragaini, Fabio; European Journal of Organic Chemistry; vol. 2017; nb. 14; (2017); p. 1902 - 1910 View in Reaxys

S S

O

Rx-ID: 9634408 View in Reaxys 3/21 Yield 80 %

Conditions & References With [hydroxy(tosyloxy)iodo]benzene in methanol, Time= 0.333333h, T= 20 °C Justik, Michael W.; Koser, Gerald F.; Tetrahedron Letters; vol. 45; nb. 32; (2004); p. 6159 - 6163 View in Reaxys

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S O

O

O

Cl S

Sn

Rx-ID: 3967722 View in Reaxys 4/21 Yield

Conditions & References

42 %

With bis-triphenylphosphine-palladium(II) chloride in benzene, react. mixt. washed (aq. KF); extn.of org. layer (ether); dried over MgSO4; product isolated by distn. (reduced pressure); acetonylated by chromy. (silica gel) Kosugi; Miyajima; Nakanishi; Sano; Migita; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3383 3385 ; (from Gmelin) View in Reaxys

42 %

With bis-triphenylphosphine-palladium(II) chloride in toluene, react. mixt. washed (aq. KF); extn.of org. layer (ether); dried over MgSO4; product isolated by distn. (reduced pressure); acetonylated by chromy. (silica gel) Kosugi; Miyajima; Nakanishi; Sano; Migita; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3383 3385 ; (from Gmelin) View in Reaxys With oxonium, bis-triphenylphosphine-palladium(II) chloride, 1.) THF, 120 deg C, Yield given. Multistep reaction Kosugi; Miyajima; Nakanishi; Sano; Migita; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3383 3385 View in Reaxys

O

O

O

S

O

S O

P O

Sn

Rx-ID: 3975439 View in Reaxys 5/21 Yield 83 %

Conditions & References With bis-triphenylphosphine-palladium(II) chloride in benzene, react. mixt. washed (aq. KF); extn.of org. layer (ether); dried over MgSO4; product isolated by distn. (reduced pressure); acetonylated by chromy. (silica gel) Kosugi; Miyajima; Nakanishi; Sano; Migita; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3383 3385 ; (from Gmelin) View in Reaxys

83 %

With bis-triphenylphosphine-palladium(II) chloride in toluene, react. mixt. washed (aq. KF); extn.of org. layer (ether); dried over MgSO4; product isolated by distn. (reduced pressure); acetonylated by chromy. (silica gel) Kosugi; Miyajima; Nakanishi; Sano; Migita; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3383 3385 ; (from Gmelin) View in Reaxys With oxonium, tetrakis(triphenylphosphine) palladium(0), 1.) HMPA, 100 deg C, 20 h, Yield given. Multistep reaction Kosugi; Miyajima; Nakanishi; Sano; Migita; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3383 3385 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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O S

S

O

O S

S

Rx-ID: 3138202 View in Reaxys 6/21 Yield

Conditions & References With hydrogenchloride in methanol, Heating, Yield given Ogura, Katsuyuki; Ohtsuki, Kazuo; Takahashi, Kazumasa; Iida, Hirotada; Chemistry Letters; (1986); p. 1597 - 1598 View in Reaxys S

S

O O

1.) tricarbonyl(η6-thiophene)chromium(0) Rx-ID: 20166183 View in Reaxys 7/21

Yield

Conditions & References Reaction Steps: 4 1: 96 percent / K2CO3 / propan-2-ol / Heating 2: 100 percent / NaBH4 / ethanol; benzene / 7 h / 50 °C 3: NaH / dimethylformamide / 1.) 0 deg C, 6 h; 2.) RT, 18 h 4: cc. HCl / methanol / Heating With hydrogenchloride, sodium tetrahydroborate, sodium hydride, potassium carbonate in methanol, ethanol, N,N-dimethyl-formamide, isopropyl alcohol, benzene Ogura, Katsuyuki; Ohtsuki, Kazuo; Takahashi, Kazumasa; Iida, Hirotada; Chemistry Letters; (1986); p. 1597 - 1598 View in Reaxys

O S

S

O

O S

S

Rx-ID: 20188457 View in Reaxys 8/21 Yield

Conditions & References Reaction Steps: 2 1: NaH / dimethylformamide / 1.) 0 deg C, 6 h; 2.) RT, 18 h 2: cc. HCl / methanol / Heating With hydrogenchloride, sodium hydride in methanol, N,N-dimethyl-formamide Ogura, Katsuyuki; Ohtsuki, Kazuo; Takahashi, Kazumasa; Iida, Hirotada; Chemistry Letters; (1986); p. 1597 - 1598 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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O S

S

O

O S

S

Rx-ID: 20200956 View in Reaxys 9/21 Yield

Conditions & References Reaction Steps: 3 1: 100 percent / NaBH4 / ethanol; benzene / 7 h / 50 °C 2: NaH / dimethylformamide / 1.) 0 deg C, 6 h; 2.) RT, 18 h 3: cc. HCl / methanol / Heating With hydrogenchloride, sodium tetrahydroborate, sodium hydride in methanol, ethanol, N,N-dimethyl-formamide, benzene Ogura, Katsuyuki; Ohtsuki, Kazuo; Takahashi, Kazumasa; Iida, Hirotada; Chemistry Letters; (1986); p. 1597 - 1598 View in Reaxys

S

S

O

O

Rx-ID: 1504187 View in Reaxys 10/21 Yield

Conditions & References

40 %

With potassium permanganate, manganese(II) acetate in acetic acid, 1.) 90 - 95 deg C, 0.5 h, 2.) 60 deg C Min, R. S.; Aksenov, V. S.; Vinogradov, M. G.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 30; nb. 10; (1981); p. 1902 - 1907; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1981); p. 2315 - 2320 View in Reaxys With manganese triacetate in acetic acid, T= 60 °C , also in the presence of benzene at 70 deg C (relative reactivity), Rate constant Vinogradova, M. G.; Min, R. S.; Aksenov, V. S.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; (1982); p. 1760 - 1765; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 9; (1982); p. 1994 - 1999 View in Reaxys

S

S

S

O O

Rx-ID: 3116191 View in Reaxys 11/21 Yield

Conditions & References

75 %

With acetic acid, zinc, Time= 1h, T= 100 °C Tamura, Yasumitsu; Choi, Hong Dae; Mizutani, Masako; Ueda, Yuko; Ishibashi, Hiroyuki; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 10; (1982); p. 3574 - 3579 View in Reaxys S O

Rx-ID: 5413857 View in Reaxys 12/21

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Yield

Conditions & References Thiophencarboxaldehyd, Et-CO-CHBr-CH3 Belcher et al.; Journal of Chemical and Engineering Data; vol. 20; (1975); p. 206 View in Reaxys 2-Chlorthiophen, K-Aceton-enolat/Photolyse Bunnett; Gloor; Heterocycles; vol. 5; (1976); p. 377,395 View in Reaxys 2-Bromthiophen, K-Aceton-enolat/Photolyse Bunnett; Gloor; Heterocycles; vol. 5; (1976); p. 377,395 View in Reaxys Thiophen, Aceton/Mn(OAc)3 Min et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 28; (1979); p. 2114; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 28; (1979); p. 2292 View in Reaxys

S

S O

O

N N

Rx-ID: 18702 View in Reaxys 13/21 Yield

Conditions & References With copper(II) sulfate Novak et al.; Collection of Czechoslovak Chemical Communications; vol. 22; (1957); p. 1836,1845 View in Reaxys -2

S

O

(v1)

O

N Cu 2+

N

O

S

(v1)

O

S O

O

Rx-ID: 5413858 View in Reaxys 14/21 Yield

Conditions & References Novak et al.; Collection of Czechoslovak Chemical Communications; vol. 22; (1957); p. 1836,1845 View in Reaxys O

S

S

O

N O

Rx-ID: 118555 View in Reaxys 15/21 Yield

Conditions & References With lithium aluminium tetrahydride, diethyl ether, T= -40 °C , anschliessendes Behandeln mit wss. Salzsaeure Gilsdorf; Nord; Journal of the American Chemical Society; vol. 74; (1952); p. 1837,1841 View in Reaxys O

S

S Cl

O

N

H

O

lithium alanate

O

Rx-ID: 5413859 View in Reaxys 16/21 Yield

Conditions & References T= -40 °C

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Gilsdorf; Nord; Journal of the American Chemical Society; vol. 74; (1952); p. 1837,1841 View in Reaxys S

O

S

OH

O

OH

O

Rx-ID: 79003 View in Reaxys 17/21 Yield

Conditions & References T= 430 - 450 °C , Leiten ueber Thoriumoxid Cagniant; Bulletin de la Societe Chimique de France; (1949); p. 847,851 View in Reaxys O S

S O

O O

Rx-ID: 241548 View in Reaxys 18/21 Yield

Conditions & References With sodium hydroxide, Erhitzen des Reaktionsprodukts auf 120grad Cagniant; Bulletin de la Societe Chimique de France; (1949); p. 847,851 View in Reaxys S

S

O O

Rx-ID: 22360638 View in Reaxys 19/21 Yield

Conditions & References Reaction Steps: 2 1: sodium; xylene 2: ethanolic NaOH-solution / Erhitzen des Reaktionsprodukts auf 120grad With sodium hydroxide, sodium, xylene Cagniant; Bulletin de la Societe Chimique de France; (1949); p. 847,851 View in Reaxys S

S

O Cl

Rx-ID: 22360676 View in Reaxys 20/21 Yield

Conditions & References Reaction Steps: 3 1: acetone; water 2: aq.-ethanolic KOH-solution 3: 430 - 450 °C / Leiten ueber Thoriumoxid With potassium hydroxide, water, acetone Cagniant; Bulletin de la Societe Chimique de France; (1949); p. 847,851 View in Reaxys Reaction Steps: 3 1: acetone; water 2: aq.-ethanolic KOH-solution 3: 430 - 450 °C / Leiten ueber Thoriumoxid

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With potassium hydroxide, water, acetone Cagniant; Bulletin de la Societe Chimique de France; (1949); p. 847,851 View in Reaxys S

S

O N

Rx-ID: 22360737 View in Reaxys 21/21 Yield

Conditions & References Reaction Steps: 2 1: aq.-ethanolic KOH-solution 2: 430 - 450 °C / Leiten ueber Thoriumoxid With potassium hydroxide Cagniant; Bulletin de la Societe Chimique de France; (1949); p. 847,851 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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