Water → Ethyl 6-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-7-hydroxyheptanoate

HRID 1921878Notes

Reaction equation

[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]

Participants

Conditions

Temperature: -10 °C

Procedure

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.

Workup

additionThen, 4.27 ml (4.27 mmol) of a 1 M borane-THF complex solution are added dropwise
extractionextracted with ethyl acetate
concentrationthe combined organic phases are concentrated
customThe resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:1, 3:1)

Sources & evidence

ORD record: ord-a2f73c2c3a684f0283439687cbbeba30
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173704B2

Reaction notes

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