Ammonium Chloride → 4-[3-(3,5-Difluoro-4-triisopropylsilanyloxybenzyl)-4-hydroxybutyl]benzonitrile

HRID 1921893Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]([CH2:15][C:16]2[CH:21]=[C:20]([F:22])[C:19]([O:23][Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])=[C:18]([F:34])[CH:17]=2)[C:12](O)=[O:13])=[CH:5][CH:4]=1)#[N:2].[Cl-].[NH4+]>C1COCC1>[F:34][C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([F:22])[C:19]=1[O:23][Si:24]([CH:25]([CH3:27])[CH3:26])([CH:28]([CH3:30])[CH3:29])[CH:31]([CH3:32])[CH3:33])[CH2:15][CH:11]([CH2:12][OH:13])[CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: -10 °C

Procedure

4879 mg (10 mmol) of 4-(4-cyanophenyl)-2-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)butanoic acid are dissolved in 244 ml of THF and cooled to −10° C. under argon. Then 20.01 ml (20.01 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 9:1→4:1→2:1→1:1). 2705 mg (57% of theory) of the title compound are obtained.

Workup

additionThen 20.01 ml (20.01 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 9:1→4:1→2:1→1:1)

Sources & evidence

ORD record: ord-dd3d14d88675464fb1d8f2c7515dbea2
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173704B2

Reaction notes

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