Methanesulfonyl chloride → HCID 20158410, compound

Participants

Reaction Steps

46 mg of 2-chloro-4-trimethylsilyloxy-4-[3-(3,4-dimethoxyphenyl)propyl]-5-(1-hydroxy-6-methoxycarbonylhexyl)-2-cyclopentenone was dissolved in 1 ml of pyridine, and 100 microliters of methanesulfonyl chloride was added. The mixture was stirred for 2.5 hours. 150 microliters of 1,8-diazabicyclo[5.4.0]undec-7-ene was added, and the mixture was stirred for 6 hours. 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. After filtration and concentration, the residue was chromatographed on a silica gel column to give 15 mg (yield 28%) of 2-chloro-4-tri-methylsilyloxy-4-[3-(3,4-dimethoxyphenyl)propyl]-5-(1-methanesulfonyloxy-6-methoxycarbonylhexyl)-2-cyclopentenone and 7.7 mg (yield 17%) of 2-chloro-4-trimethylsilyloxy-4-[3-(3,4-dimethoxyphenyl)propyl]-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone.

Provenance & Evidence