(4S)-HYDROXY-3-METHYL-2-(2-PROPENYL)-2-CYCLOPENTENE-1-ONE synthesis
- Product Name:(4S)-HYDROXY-3-METHYL-2-(2-PROPENYL)-2-CYCLOPENTENE-1-ONE
- CAS Number:22373-75-7
- Molecular formula:C9H12O2
- Molecular Weight:152.19
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Yield:-
Reaction Conditions:
with boron trichloride in dichloromethane;
Steps:
(4S) 2-allyl-3-methyl-4-hydroxy-2-cyclopentene-1-one
(4S) 2-allyl-3-methyl-4-hydroxy-2-cyclopentene-1-one 1.5 g of (4S) 2-allyl-3-methyl-2-cyclopentene-1-one-4-yl 2,2-dimethyl-3R-(2-methyl-1-propenyl)-cyclopropane-1R-carboxylate was added to 15 ml of methylene chloride and then 7.8 ml of a methylene chloride solution of 1.6 M of boron trichloride was slowly added to the mixture at -20° C. The mixture was stirred at -12° C. for 3 hours and was then poured into an ice-water mixture. The mixture was stirred for 15 hours and the pH was adjusted to 10 by addition of dilute sodium hydroxide. The aqueous phase was saturated with sodium chloride and was then extracted with methylene chloride. The organic phase was dried and evaporated to dryness and the residue was chromatographed over silica gel. Elution with a 7-3 benzene ethyl acetate mixture yielded 530 mg of (4S) 2-allyl-3-methyl-4-hydroxy-2-cyclopentene-1-one with a specific rotation of [α]D20 =+5° (c=1.2% in benzene).
References:
US4307251,1981,A
