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O
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Date
13 reactions in Reaxys
2018-05-11 16h:44m:03s (UTC)
O
Search as: Product, As drawn, No mixtures ))
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2018-05-11 16:44:50
HO
O
O
O
Rx-ID: 26050515 View in Reaxys 1/13 Yield
Conditions & References
99 %
With dipyridinium dichromate in dichloromethane, Time= 2h, T= 20 °C Benniston, Andrew C.; Fortage, Jerome; Tetrahedron Letters; vol. 49; nb. 27; (2008); p. 4292 - 4295 View in Reaxys
75 %
STEP-3: Synthesis of 1-methoxy-2-naphthaldehyde. PCC (19 g, 88 mmol) with celite powder was added to the (1-methoxy-naphthalen-2-yl)-methanol (15 g, 80 mmol) in DCM (500 ml) at room temperature. The reaction mixture was stirred at room temperature for 1 h. Solid material was filtered off. The filtrate wasconcentrated, chromatographed (silica gel 100-200 mesh, 15percent ethylacetate-hexane) affording 1-methoxy- 2-naphthaldehyde (11g, 75percent). 1H-NMR (CDCl3, 500 MHz) d4.02 (s, 3H), 7.18 (s, 1H), 7.37 (m, 1H), 7.53 (m, 1H), 7.73 (d, J = 8.3 Hz,1H), 7.87 (d, J = 8.3 Hz, 1H), 8.35 (s, 1H), 10.56 (s, 1H). With pyridinium chlorochromate in dichloromethane, Time= 1h, T= 20 °C Ganguly, Aniruddha; Ghosh, Soumen; Kar, Samiran; Guchhait, Nikhil; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 143; (2015); p. 72 - 80 View in Reaxys With manganese(IV) oxide in tetrahydrofuran, Time= 4h, Inert atmosphere, Reflux Kaga, Atsushi; Hayashi, Hirohito; Hakamata, Hiroyuki; Oi, Miku; Uchiyama, Masanobu; Takita, Ryo; Chiba, Shunsuke; Angewandte Chemie - International Edition; vol. 56; nb. 39; (2017); p. 11807 - 11811; Angew. Chem.; vol. 129; (2017); p. 11969 - 11973,5 View in Reaxys
I
O
O
O
OH
Rx-ID: 42894308 View in Reaxys 2/13 Yield 91 %
Conditions & References With potassium carbonate in N,N-dimethyl-formamide, Time= 15h, T= 20 °C , Inert atmosphere Saito, Hiromu; Uchida, Akira; Watanabe, Soichiro; Journal of Organic Chemistry; vol. 82; nb. 11; (2017); p. 5663 - 5668 View in Reaxys
80 %
1 : 1-methoxy-2-naphthaldehyde (S6) To a stirred solution of 193 mg (1.12 mmol, 1.0 eq) 1-hydroxy-2-naphthaldehyde (TCI America) dissolved in 5 mL N,N-dimethylformamide at 0° C. was added 49.0 mg (1.23 mmol, 1.2 eq) sodium hydride. The mixture was stirred at 0° C. for 5 min and 140 μL (2.24 mmol, 2.0 eq) methyl iodide was added. The reaction was heated to 60° C. and stirred for 3 h. The reaction was partitioned between ethyl acetate and water, the organic layer washed with water (1×), brine (2×), and dried (MgSO4). The organic layer was concentrated and the residue purified by flash chromatography with a 0-20percent ethyl acetate in hexane gradient to provide 165 mg (80percent) of product as a light brown solid. 1H-NMR (400 MHz, CDCl3) δ 10.59 (d, J=0.76 Hz, 1H), 8.23 (d, J=8.16 Hz, 1H), 7.86-7.82 (m, 2H), 7.64-7.54 (m, 3H), 4.12 (s, 3H); 13C-NMR (100 MHz) δ 189.6, 162.6, 138.1, 129.4, 128.4, 127.9, 126.9, 124.9, 124.7, 123.2, 122.7, 65.7; LRMS calculated for C12H10O2 (M+H)+ m/z: 1187.1, measured 187.1. Stage 1: With sodium hydride in N,N-dimethyl-formamide, Time= 0.0833333h, T= 0 °C Stage 2: in N,N-dimethyl-formamide, Time= 3h, T= 0 - 60 °C Patent; Vanderbilt University; Skaar, Eric P.; Surdel, Matthew; Sulikowski, Gary A.; Dutter, Brendan; Reid, Paul; Waterson, Alex; (62 pag.); US2016/213780; (2016); (A1) English
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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View in Reaxys
O
O
OH
Rx-ID: 45521319 View in Reaxys 3/13 Yield
Conditions & References Reaction Steps: 2 1: magnesium chloride; triethylamine / acetonitrile 2: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere With potassium carbonate, triethylamine, magnesium chloride in N,N-dimethyl-formamide, acetonitrile Saito, Hiromu; Uchida, Akira; Watanabe, Soichiro; Journal of Organic Chemistry; vol. 82; nb. 11; (2017); p. 5663 - 5668 View in Reaxys
I
O
HO
O
O
OH
Rx-ID: 43465574 View in Reaxys 4/13 Yield 57 %
Conditions & References Stage 1: With potassium carbonate in N,N-dimethyl-formamide, Time= 120h, T= 45 °C Stage 2: With diisobutylaluminium hydride in tetrahydrofuran, Time= 20h, T= 0 - 20 °C , Inert atmosphere Stage 3: With pyridinium chlorochromate in 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran, T= 20 °C Basak, Tymoteusz; Grudzień, Krzysztof; Barbasiewicz, Michał; European Journal of Inorganic Chemistry; vol. 2016; nb. 21; (2016); p. 3513 - 3523 View in Reaxys
HO
O
O
Cl
O
Rx-ID: 39738502 View in Reaxys 5/13 Yield 56 %
Conditions & References Typical experimental procedure: General procedure: To a stirred solution of substrate (1 mmol, arylhalide/olefinic halide) in suitable alcohol (MeOH/EtOH, 10 mL), sodiumcarbonate (1.06 g, 2 mol percent) was added and the reaction mixture was refluxed(MeOH = 65 C/EtOH = 78 C) for specified time. On completion, the reactionmixture was filtered, washed with methanol and dried in vacuo. The residuewas taken in ethyl acetate (20 mL) and washed with water. Organic layer wasdried over anhydrous sodium sulfate and evaporated in vacuo. The residuethus obtained was purified through Flash chromatography using ethyl acetate–hexane system. All the compounds were characterized and confirmed bycomparison of their spectral data and physical properties with reportedliterature With sodium carbonate, Time= 4h, T= 65 °C Kumar, Balagani Sathish; Negi, Arvind S.; Tetrahedron Letters; vol. 56; nb. 18; (2015); p. 2340 - 2344 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
O
O
O
O
Rx-ID: 39907992 View in Reaxys 6/13 Yield
Conditions & References Reaction Steps: 2 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Reflux 2: pyridinium chlorochromate / dichloromethane / 1 h / 20 °C With lithium aluminium tetrahydride, pyridinium chlorochromate in tetrahydrofuran, dichloromethane Ganguly, Aniruddha; Ghosh, Soumen; Kar, Samiran; Guchhait, Nikhil; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 143; (2015); p. 72 - 80 View in Reaxys
O
HO
O
O
OH
Rx-ID: 39907997 View in Reaxys 7/13 Yield
Conditions & References Reaction Steps: 3 1: potassium carbonate / acetone / 18 h / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Reflux 3: pyridinium chlorochromate / dichloromethane / 1 h / 20 °C With lithium aluminium tetrahydride, potassium carbonate, pyridinium chlorochromate in tetrahydrofuran, dichloromethane, acetone Ganguly, Aniruddha; Ghosh, Soumen; Kar, Samiran; Guchhait, Nikhil; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 143; (2015); p. 72 - 80 View in Reaxys
N
O
O
O
O
O O
Rx-ID: 9892143 View in Reaxys 8/13 Yield
Conditions & References
57 %, 6.3 % Stage 1: With n-butyllithium, N,N,N,N,-tetramethylethylenediamine in hexane, cyclohexane, Time= 2h, T= 20 °C Stage 2: in hexane, cyclohexane, cooling Giurg; Syper; Mlochowski; Polish Journal of Chemistry; vol. 78; nb. 2; (2004); p. 231 - 238 View in Reaxys N N N O
O
O
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.
4/6
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O
O
O NH
O
O
O
O N
Rx-ID: 3217968 View in Reaxys 9/13 Yield
Conditions & References
1.5 %, 1.1 %, 61 %
in various solvent(s), Time= 0.166667h, T= 230 °C Watanabe; Takahashi; Kamakura; Sakaguchi; Osaki; Toyama; Mizuma; Ueda; Murakami; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 12; (1991); p. 3145 - 3152 View in Reaxys
O
O
O
O
O
O
O
O
Rx-ID: 2203475 View in Reaxys 10/13 Yield
Conditions & References
15 %, 39 %, With potassium dichromate, mercury(II) propionate, trifluoroacetic acid in 1,4-dioxane, water, Time= 20h, Ambient tempera7% ture Boddy, Ian K.; Cambie, Richard C.; Dixon, Graham; Rutledge, Peter S.; Woodgate, Paul D.; Australian Journal of Chemistry; vol. 36; nb. 4; (1983); p. 803 - 813 View in Reaxys 15 %, 39 %, With potassium dichromate, mercury(II) propionate, trifluoroacetic acid in 1,4-dioxane, water, Time= 20h, Ambient tempera7% ture Boddy, Ian K.; Cambie, Richard C.; Dixon, Graham; Rutledge, Peter S.; Woodgate, Paul D.; Australian Journal of Chemistry; vol. 36; nb. 4; (1983); p. 803 - 813 View in Reaxys
O
N O
O
O
Rx-ID: 4323564 View in Reaxys 11/13 Yield
Conditions & References (i) nBuLi, (ii) /BRN= 636496/, Multistep reaction Narasimhan,N.S.; Mali,R.S.; Tetrahedron; vol. 31; (1975); p. 1005 - 1009 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.
5/6
2018-05-11 16:44:50
O
O
Rx-ID: 7184993 View in Reaxys 12/13 Yield
Conditions & References Das Gupta; Chatterje; Indian Journal of Chemistry; vol. 11; (1973); p. 707 View in Reaxys Das Gupta; Chatterje; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1973); p. 1802,1805 View in Reaxys Wolter; Kosler; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 10; (1970); p. 401,402 View in Reaxys
O
O
1-oxy-naphthaldehyde-(2)
S O
O
O
O
Rx-ID: 7184994 View in Reaxys 13/13 Yield
Conditions & References With alkali Bezdzik; Friedlaender; Monatshefte fuer Chemie; vol. 30; (1909); p. 280 View in Reaxys Friedlaender; Chemische Berichte; vol. 41; (1908); p. 1038 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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