3,3-Dimethylcyclopentan-1-one → 3,3-Dimethyl-1-vinylcyclopentanol

Participants

Reaction Conditions

Reaction Steps

The reactor was charged with vinylmagnesium bromide (0.6M in THF, 245 ml, 147 mmol) and the solution was cooled to 5-10° C. 3,3-Dimethylcyclopentanone (2a, 15.0 g, 134 mmol) in THF (50 ml) was added over 10 minutes while keeping the temperature of the reaction mixture between 5-10° C. by means of an ice bath. The mixture was stirred for 30 minutes, then quenched with 10% AcOH (150 ml) and extracted with hexane (2×100 ml). The combined organic phases were washed with water, dried (MgSO4), concentrated and distilled bulb-to-bulb to afford 3a (14.3 g, 76% yield) as a colorless liquid.

Provenance & Evidence