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

HRID 1921885Notizen

Reaktionsgleichung

[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

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

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.

Aufarbeitung

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)

Quellen und Nachweise

ORD-Eintrag: ord-27c563ef1bd54ad49ea1865950bb5fe8
Quelldatensatz: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08173704B2

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