Water → Ethyl 6-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-7-hydroxyheptanoate
반응식
[CH2:1]([O:3][C:4](=[O:33])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([CH2:13][C:14]1[CH:19]=[C:18]([F:20])[C:17]([O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[C:16]([F:32])[CH:15]=1)[C:10](O)=[O:11])[CH3:2].O>C1COCC1>[F:32][C:16]1[CH:15]=[C:14]([CH:19]=[C:18]([F:20])[C:17]=1[O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:23]([CH3:25])[CH3:24])[CH:26]([CH3:28])[CH3:27])[CH2:13][CH:9]([CH2:10][OH:11])[CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:33]참가 물질
4
반응 조건
- 온도
- -10 °C
실험 절차
1.6 g (3.29 mmol) of 2-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)heptanedioic acid 7-ethyl ester are dissolved in 30 ml of THF and cooled to −10° C. under argon. Then, 4.27 ml (4.27 mmol) of a 1 M borane-THF complex solution are added dropwise, and the mixture is stirred at 0° C. until reaction is complete. The mixture is hydrolyzed with water and extracted with ethyl acetate, and the combined organic phases are concentrated. The resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:1, 3:1). 1.18 g (76% of theory) of the title compound are obtained.