Sodium hydride → trifluoro-methanesulfonic acid (R)-2,2,3,3,3-pentafluoro-1-(4-fluorophenyl)propyl ester
反応式
[H-].[Na+].[F:3][C:4]([F:18])([C:14]([F:17])([F:16])[F:15])[C@@H:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)[OH:6].[F:19][C:20]([F:26])([F:25])[S:21](Cl)(=[O:23])=[O:22]>C(OCC)C>[F:18][C:4]([F:3])([C:14]([F:15])([F:16])[F:17])[C@H:5]([O:6][S:21]([C:20]([F:26])([F:25])[F:19])(=[O:23])=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1参加物
反応条件
- 温度
- 0 °C
実験手順
A 60% suspension of NaH in oil (2.35 g, 58.8 mmol) was washed several times with hexanes and after suspending it in anhydrous ethyl ether (100 mL), (R)-2,2,3,3,3-pentafluoro-1-(4-fluoro-phenyl)propan-1-ol (12.0 g, 49 mmol) in ether (20 mL) was added slowly at room temperature. After stirring for 15 min, the reaction mixture was cooled at 0° C. and trifluoromethylsulfonyl chloride (12.38 g, 73.7 mmol) was added. The reaction mixture was stirred for 1:30 h at 0° C., then concentrated under reduced pressure and the residue was diluted with hexane (100 mL). The reaction mixture was washed with sat. sol. NaHCO3, brine and dried over magnesium sulfate. After removing the solvent on rotovapor, trifluoro-methanesulfonic acid (R)-2,2,3,3,3-pentafluoro-1-(4-fluorophenyl)propyl ester was obtained as a colorless oil (16.0 g).
後処理
- stirringThe reaction mixture was stirred for 1
- concentration30 h at 0° C., then concentrated under reduced pressure
- additionthe residue was diluted with hexane (100 mL)
- washThe reaction mixture was washed with sat. sol. NaHCO3, brine
- dry with materialdried over magnesium sulfate
- customAfter removing the solvent on rotovapor
出典と根拠
- ORDレコード
- ord-0996aabc028f4af5b2ed5d5e2893a086
- 出典データセット
- uspto-grants-2011_02
- 特許番号
- US07893093B2
反応ノート
読み込み中…