3-Ethyl-3-methylcyclopentanone → 3-Ethyl-3-methyl-1-vinylcyclopentanol

HRID 516277Notes

Reaction equation

HRID 516277 reaction equation
[CH2:1]([C:3]1([CH3:9])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4]1)[CH3:2].[CH:10]([Mg]Br)=[CH2:11]>>[CH2:1]([C:3]1([CH3:9])[CH2:7][CH2:6][C:5]([CH:10]=[CH2:11])([OH:8])[CH2:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 217186343-Ethyl-3-methylcyclopentanoneHCID 178418507HCID 178418507, compound

Product 1

HCID 894289063-Ethyl-3-methyl-1-vinylcyclopentanolYield 60%

Procedure

3-Ethyl-3-methylcyclopentanone (2b, 30.0 g, 0.24 mol) was reacted with vinylmagnesium bromide (0.6M in THF, 285 ml, 0.29 mol), as described in Example 1b, to afford 3b (22.0 g, 2:1 mixture of diastereomers, 60% yield) as a colorless liquid.

Sources & evidence

ORD record
ord-1292d29f1d55408786b1e4c6a4b314be
Source dataset
uspto-grants-2015_08
Patent number
US09109186B2

Reaction notes

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