Sodium Hydroxide → (2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionic acid
反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:30])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])=[CH:18][CH:17]=2)[C:10]([O:12]CC)=[O:11])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>O1CCCC1CCO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:30])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:23]([F:28])([F:29])[C:24]([F:26])([F:27])[F:25])=[CH:18][CH:17]=2)[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1参加物
4
反応物 2
生成物 1
試薬・触媒・溶媒 1
実験手順
To a solution of ethyl (2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionate (3.84 g, 8.52 mmol) in tetrahydrofuran-ethanol (20 ml—20 ml) was added 1N sodium hydroxide (17 ml, 17 mmol) at room temperature, and the mixture was stirred overnight at room temperature. After completion of the reaction, the organic solvent was evaporated under reduced pressure, and the aqueous layer was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give (2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionic acid (2.85 g, 79%) as colorless crystals.