2-Cyclopenten-1-one → HCID 69338188, compound

Participants

Reaction Steps

44 mg of cyclopentenone and 492 mg of benzyl 2,2,2-trichloroacetimidate (Aldrich, 14,033-3) was dissolved in 2.5 ml of dichloromethane (Wako Pure Chemical Industries, 135-02441) under argon flow. 1 ml of 28 μl/ml boron trifluoride diethyl ether complex (Wako Pure Chemical Industries, 022-08362) solution in dichloromethane was slowly added thereto while stirring. After stirring for 8 hours at room temperature, the mixture was concentrated under reduced pressure. The concentrate was subjected to silica gel thin-layer chromatography using chloroform:methanol=19:1 as a developing solvent to purify 4-benzylcyclopentenone ether, 5-benzylcyclopentenone ether and 4,5-dibenzylcyclopentenone ether. The Rf values for 4-benzylcyclopentenone ether, 5-benzylcyclopentenone ether and 4,5-dibenzylcyclopentenone ether were 0.3, 0.45 and 0.8, respectively. The yields of 4-benzylcyclopentenone ether, 5-benzylcyclopentenone ether and 4,5-dibenzylcyclopentenone ether were 3.7%, 3.7% and 2.5%, respectively.

Provenance & Evidence