3-Methoxycyclohex-2-en-1-one → 3-Butylcyclohex-2-en-1-one

HRID 1006184Notes

Reaction equation

HRID 1006184 reaction equation
CO[C:3]1[CH2:8][CH2:7][CH2:6][C:5](=[O:9])[CH:4]=1.[Li][CH2:11][CH2:12][CH2:13][CH3:14]>C(OCC)(=O)C>[CH2:11]([C:3]1[CH2:8][CH2:7][CH2:6][C:5](=[O:9])[CH:4]=1)[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 855973-Methoxycyclohex-2-en-1-oneHCID 178418339Butyllithium

Product 1

HCID 2390953-Butylcyclohex-2-en-1-oneYield 97.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The general procedure for the preparation of substrates using 3-methoxycyclohexenone (1.26 g, 10 mmol) and n-BuLi (20 mmol, 1.6 M in hexane) gave, after flash chromatography (4:1 hexanes:ethyl acetate) the title compound as a colorless liquid (1.48 g, 97%). Spectroscopic data were consistent with previously reported data for this compound.2

Workup

  1. customThe general procedure for the preparation of substrates
  2. customgave

Sources & evidence

ORD record
ord-79012498f96c4523b95f6a25de9f0d83
Source dataset
uspto-grants-2004_09
Patent number
US06787655B2

Reaction notes

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