2-Cyclopenten-1-one → HCID 69338281, compound

Participants

Reaction Steps

Cyclopentenone (44 mg) and 287 mg of tert-butyl 2,2,2-trichloroacetimidate (manufactured by Aldrich, 36,478-9) were dissolved in 2.5 ml of dichloromethane in an argon stream. To this was gradually added 1 ml of a solution of 28 μl/ml of boron trifluoride-diethyl ether complex in dichloromethane with stirring. The mixture was stirred at room temperature for eight hors, concentrated in vacuo and subjected to a silica gel thin layer chromatography by the same manner as in Example 1- (2) to purify 4-tert-butylcyclopentenone ether, 5-tert-butylcyclopentenone ether and 4,5-di-tert-butylcyclopentenone ether. The Rf values of 4-tert-butylcyclopentenone ether, 5-tert-butylcyclopentenone ether and 4,5-di-tert-butylcyclopentenone ether were 0.35, 0.27 and 0.73, respectively. Yields of 4-tert-butylcyclopentenone ether, 5-tert-butylcyclopentenone ether and 4,5-di-tert-butylcyclopentenone ether were 9.2%, 1.9% and 11%, respectively.

Provenance & Evidence