Ammonium Chloride → Methyl 4-[3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-4-hydroxybutyl]benzoate

HRID 1921885Notes

Reaction equation

[C:1]([CH:4]([CH2:17][C:18]1[CH:23]=[C:22]([F:24])[C:21]([O:25][Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[C:20]([F:36])[CH:19]=1)[CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)(O)=[O:2].[Cl-].[NH4+]>C1COCC1>[F:36][C:20]1[CH:19]=[C:18]([CH:23]=[C:22]([F:24])[C:21]=1[O:25][Si:26]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:33]([CH3:34])[CH3:35])[CH2:17][CH:4]([CH2:1][OH:2])[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: -10 °C

Procedure

4.2 g (8.07 mmol) of methyl 4-[3-carboxy-4-(3,5-difluoro-4-triisopropylsilanyloxyphenyl)butyl]-benzoate are dissolved in 200 ml of THF and cooled to −10° C. under argon. Then 16.13 ml (16.13 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 saturated ammonium chloride solution and extracted with diethyl ether, and the combined organic phases are concentrated. The resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1→10:1→4:1). 2.92 g (71% of theory) of the title compound are obtained.

Workup

additionThen 16.13 ml (16.13 mmol) of a 1 M borane-THF complex solution are added dropwise
extractionextracted with diethyl ether
concentrationthe combined organic phases are concentrated
customThe resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1→10:1→4:1)

Sources & evidence

ORD record: ord-27c563ef1bd54ad49ea1865950bb5fe8
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173704B2

Reaction notes

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