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

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Reaction Steps

44 mg of cyclopentenone and 287 mg of t-butyl 2,2,2-trichloroacetimidate (Aldrich, 36,478-9) was dissolved in 2.5 ml of dichloromethane under argon flow. 1 ml of 28 μl/ml boron trifluoride diethyl ether complex 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 to purify 4-t-butylcyclopentenone ether, 5-t-butylcyclopentenone ether and 4,5-di-t-butylcyclopentenone ether as described in Referential Example 1-(21). The Rf values for 4-t-butylcyclopentenone ether, 5-t-butylcyclopentenone ether and 4,5-di-t-butylcyclopentenone ether were 0.35, 0.27 and 0.73, respectively. The yields of 4-t-butylcyclopentenone ether, 5-t-butylcyclopentenone ether and 4,5-di-t-butylcyclopentenone ether were 9.2%, 1.9% and 11%, respectively.

Provenance & Evidence