Methanesulfonyl chloride → HCID 13754718, compound

Participants

Reaction Steps

40 mg (0.13 mmole) of 4-butyl-5-(1-hydroxybutyl)-4-trimethylsilyloxy-2-cyclopentenone was dissolved in 2 ml of pyridine, and at room temperature, 0.1 ml (1.3 mmoles) of mesyl chloride was added. The mixture was stirred for 8 hours. After the reaction, water was added, and the mixture was extracted with methylene chloride. The extract was dried, and concentrated, and 2 ml of benzene and 0.2 ml (1.3 mmoles) of DBU were added. The mixture was stirred at room temperature for 2 hours. Water was added, and the mixture was exracted with benzene. The extract was dried and concentrated, and the residue was chromatographed on a silica gel column (Merck silica gel 4 g, hexane:ethyl acetate=20:1) to give 18 mg (yield 48%) of 4-butyl-5-[(E)-butylidene]-4-trimethylsilyloxy-2-cyclopentenone (Rf=0.7, hexane:ethyl actate=3:1) and 5 mg (yield 14%) of its Z-isomer (Rf=0.75, hexane:ethyl acetate=3:1).

Provenance & Evidence