1-Acetylcyclohexene → 2-(1-Cyclohexenyl)-2-butanol

HRID 432065

Reaction equation

C([Zn][CH2:4][CH3:5])C.[C:6]1([C:12](=[O:14])[CH3:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]=1>>[C:6]1([C:12]([OH:14])([CH2:4][CH3:5])[CH3:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]=1

Participants

Reactant 2

HCID 136121-Acetylcyclohexene

HCID 178418750HCID 178418750, compound

Product 1

HCID 101250812-(1-Cyclohexenyl)-2-butanolYield 56%

Procedure

Diethylzinc addition to 1-(1-cyclohexenyl)-ethanone (1.04 mL, 8.05 mmol) was performed according to general procedure A using 2 mol % of Compound B enantiomer (88 mg). The product was purified by column chromatography (hexanes/EtOAc: 96/4) to give 697.1 mg of 9 (56% yield, 96% ee) of a colorless oil: [60 ]D 20=+5.9 (c 3.0, MeOH). [Published [α]D 20=+0.7 (c 3.0, MeOH, 51% ee)].

Workup

customThe product was purified by column chromatography (hexanes/EtOAc: 96/4)

Sources & evidence

ORD record: ord-e756d219a0af428290addef8bd61e8fc
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660884B2

Linked notes

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