Toluene → (E)-4-Cyclohexyl-2-(4-methanesulfonyl-phenyl)-but-2-en-1-ol

HRID 2103589Notes

Reaction equation

C([O:3][C:4](=O)/[C:5](/[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)=[CH:6]/[CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)C.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1>>[CH:8]1([CH2:7]/[CH:6]=[C:5](\[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)/[CH2:4][OH:3])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Reactant 3

HCID 1140Toluene

HCID 14487Diisobutylaluminum hydride

HCID 67084356(E)-4-Cyclohexyl-2-(4-methanesulfonyl-phenyl)-but-2-enoic acid ethyl ester

Product 1

HCID 67084508(E)-4-Cyclohexyl-2-(4-methanesulfonyl-phenyl)-but-2-en-1-olYield 79.1%

Procedure

Following the method of example 54e, using (E)-4-cyclohexyl-2-(4-methanesulfonyl-phenyl)-but-2-enoic acid ethyl ester (956 mg, 2.73 mmol) and 3 h at ambient temperature after the addition of DIBAL in toluene (4.95 mL, 6.0 mmol) gives the title compound as an amorphous solid (666 mg). MS (m/e): 291 ([M−H2O]+H).

Workup

customat ambient temperature

Sources & evidence

ORD record: ord-6a03a8bf7da74ec4b257bcc0873a1da2
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576108B2

Reaction notes

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