Methanesulfonyl chloride → HCID 13784730, compound

Participants

Reaction Steps

22 mg (44 micromoles) of 2-chloro-4-(3,7-dimethyloctyl)-5-(1-hydroxy-6-methoxycarbonyl)-4-trimethylsilyloxy-2-cyclopentenone obtained in Example 4 was dissolved in 500 microliters of pyridine, and 50 microliters (646 micromoles) of methanesulfonyl chloride was added. The mixture was stirred for 1.5 hours. 200 microliters (1.34 mmoles) of 1,8-diazabicyclo[5.4.0]undec-7-ene was added, and the mixture was stirred for 30 minutes. A saturated aqueous solution of potassium hydrogen sulfate was added, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed successively with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was chromatographed on a thin silica gel layer to give 6.3 mg (yield 30%) of 2-chloro-4-(3,7-dimethyloctyl)-5-[(Z)-6-methoxycarbonylhexylidene]-4-trimethylsilyloxy-2-cyclopentenone and 11.0 mg (yield 52%) of 2-chloro-4 -(3,7-dimethyloctyl)-5-[(E)-6-methoxycarbonylhexylidene]-4-trimethylsilyloxy-2-cyclopentenone.

Provenance & Evidence