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7 reactions in Reaxys
2018-05-11 16h:49m:52s (UTC)
O
1. Query O
Search as: Product, As drawn, No mixtures ))
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O
N
O O
O
Rx-ID: 28767405 View in Reaxys 1/7 Yield 75 %
Conditions & References Stage 1: With n-butyllithium in tetrahydrofuran, T= -78 °C Stage 2:Time= 1h, T= -78 - 20 °C , regioselective reaction Chiurato, Matteo; Routier, Sylvain; Troin, Yves; Guillaumet, Gerald; European Journal of Organic Chemistry; nb. 18; (2009); p. 3011 - 3021 View in Reaxys
60 %
8 :Compound VI-1 (5mmol, 1equiv) was dissolved in 20mL dry THF,The reaction of nitrogen cooling protection to - 78 ,Into nbutyllithium (15mmol, 3equiv),The reaction was stirred at -78 environment after one hour was warmed to 0 ,Slowly into the dry DMF (10mmol, 2equiv),The reaction is then stirred at room temperature overnight,After the reaction was quenched with water,3 times with 100mL dichloromethane extracts,Experiments with a saturated aqueous organic phase was washed,After adding anhydrous sodium sulfate and spin dry,A silica gel column (PE: EA = 10: 1),To give Compound VII-1 (60percent); Stage 1: With n-butyllithium in tetrahydrofuran, Time= 1h, T= -78 °C , Inert atmosphere Stage 2: in tetrahydrofuran, T= 0 - 20 °C , Inert atmosphere Patent; East China University of Science and Technology; Wang, Limin; Wu, Xunshen; Yang, Yang; Wu, Shengying; Wang, Feng; Wang, Guifeng; Tian, He; Wang, Zhenyan; Chen, Lirong; Huang, Zhuo; (22 pag.); CN105601608; (2016); (A) Chinese View in Reaxys
OH
O
O
O
Rx-ID: 2154803 View in Reaxys 2/7 Yield 97 %
Conditions & References With sodium acetate, pyridinium chlorochromate in dichloromethane, Time= 3h, T= 20 °C , Inert atmosphere, Molecular sieve Oslund, Rob C.; Cermak, Nathan; Gelb, Michael H.; Journal of Medicinal Chemistry; vol. 51; nb. 15; (2008); p. 4708 - 4714 View in Reaxys
92 %
With tetrapropylammonium perruthennate, 4-methylmorpholine N-oxide in dichloromethane Sawyer, J. Scott; Beight, Douglas W.; Smith, Edward C. R.; Snyder, David W.; Chastain, Marcia K.; Tielking, Richard L.; Hartley, Lawrence W.; Carlson, Donald G.; Journal of Medicinal Chemistry; vol. 48; nb. 3; (2005); p. 893 - 896 View in Reaxys
86 %
With 2,2,6,6-tetramethyl-piperidine-N-oxyl, N-chloro-succinimide, tetrabutyl-ammonium chloride, sodium hydrogencarbonate, sodium carbonate in dichloromethane, water, Time= 2h, T= 20 °C Lucas, Simon; Heim, Ralf; Negri, Matthias; Antes, Iris; Ries, Christina; Schewe, Katarzyna E.; Bisi, Alessandra; Gobbi, Silvia; Hartmann, Rolf W.; Journal of Medicinal Chemistry; vol. 51; nb. 19; (2008); p. 6138 - 6149 View in Reaxys
85 %
With Dess-Martin periodane in dichloromethane, Time= 0.5h, T= 0 - 20 °C Legouin, Beatrice; Gayral, Maud; Uriac, Philippe; Cupif, Jean-Francois; Levoin, Nicolas; Toupet, Loic; Van De Weghe, Pierre; European Journal of Organic Chemistry; nb. 28; (2010); p. 5503 - 5508 View in Reaxys
82 %
With 4 A molecular sieve, sodium acetate, pyridinium chlorochromate in dichloromethane, Time= 0.666667h
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Wu, Kun-Chan; Lin, Yu-Shan; Yeh, Yu-Shan; Chen, Chun-Yen; Ahmed, Moawia O.; Chou, Pi-Tai; Hon, Yung-Son; Tetrahedron; vol. 60; nb. 51; (2004); p. 11861 - 11868 View in Reaxys 76 %
With pyridinium chlorochromate in dichloromethane, Time= 3h, Ambient temperature Batt; Maynard; Petraitis; Shaw; Galbraith; Harris; Journal of Medicinal Chemistry; vol. 33; nb. 1; (1990); p. 360 - 370 View in Reaxys O
HO
O O
O
Rx-ID: 13198511 View in Reaxys 3/7 Yield
Conditions & References Reaction Steps: 3 1: 91 percent / Cs2CO3 / 32 h / Heating 2: 93 percent / LiAlH4 / tetrahydrofuran / 3 h / 20 °C 3: 92 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH2Cl2 With lithium aluminium tetrahydride, tetrapropylammonium perruthennate, caesium carbonate, 4-methylmorpholine N-oxide in tetrahydrofuran, dichloromethane Sawyer, J. Scott; Beight, Douglas W.; Smith, Edward C. R.; Snyder, David W.; Chastain, Marcia K.; Tielking, Richard L.; Hartley, Lawrence W.; Carlson, Donald G.; Journal of Medicinal Chemistry; vol. 48; nb. 3; (2005); p. 893 - 896 View in Reaxys Reaction Steps: 3 1: 89 percent / potassium carbonate; 18-crown-6 ether / acetone / 12 h / Heating 2: 87 percent / LiAlH4 / tetrahydrofuran / 6 h / 20 °C 3: 82 percent / pyridinium chlorochromate; sodium acetate; molecular sieves 4 Angstroem / CH2Cl2 / 0.67 h With lithium aluminium tetrahydride, 18-crown-6 ether, 4 A molecular sieve, sodium acetate, potassium carbonate, pyridinium chlorochromate in tetrahydrofuran, dichloromethane, acetone Wu, Kun-Chan; Lin, Yu-Shan; Yeh, Yu-Shan; Chen, Chun-Yen; Ahmed, Moawia O.; Chou, Pi-Tai; Hon, Yung-Son; Tetrahedron; vol. 60; nb. 51; (2004); p. 11861 - 11868 View in Reaxys
O
O
O O
O
Rx-ID: 13207369 View in Reaxys 4/7 Yield
Conditions & References Reaction Steps: 2 1: 93 percent / LiAlH4 / tetrahydrofuran / 3 h / 20 °C 2: 92 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH2Cl2 With lithium aluminium tetrahydride, tetrapropylammonium perruthennate, 4-methylmorpholine N-oxide in tetrahydrofuran, dichloromethane Sawyer, J. Scott; Beight, Douglas W.; Smith, Edward C. R.; Snyder, David W.; Chastain, Marcia K.; Tielking, Richard L.; Hartley, Lawrence W.; Carlson, Donald G.; Journal of Medicinal Chemistry; vol. 48; nb. 3; (2005); p. 893 - 896 View in Reaxys Reaction Steps: 2 1: 87 percent / LiAlH4 / tetrahydrofuran / 6 h / 20 °C
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2: 82 percent / pyridinium chlorochromate; sodium acetate; molecular sieves 4 Angstroem / CH2Cl2 / 0.67 h With lithium aluminium tetrahydride, 4 A molecular sieve, sodium acetate, pyridinium chlorochromate in tetrahydrofuran, dichloromethane Wu, Kun-Chan; Lin, Yu-Shan; Yeh, Yu-Shan; Chen, Chun-Yen; Ahmed, Moawia O.; Chou, Pi-Tai; Hon, Yung-Son; Tetrahedron; vol. 60; nb. 51; (2004); p. 11861 - 11868 View in Reaxys O
N O
O
O
Rx-ID: 4323546 View in Reaxys 5/7 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
O O
O
NH O
HN S
O
O
Rx-ID: 521627 View in Reaxys 6/7 Yield
Conditions & References With sodium carbonate, diethylene glycol Woodcock; Davies; Journal of the Chemical Society; (1958); p. 4723,4726 View in Reaxys
O O
O
NH O
HN S
O
O
Rx-ID: 519290 View in Reaxys 7/7 Yield
Conditions & References With sodium carbonate, ethylene glycol Huisgen; Nakaten; Justus Liebigs Annalen der Chemie; vol. 586; (1954); p. 84,107 View in Reaxys
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