Triethylamine → HCID 86624770, compound

Participants

Reaction Conditions

Reaction Steps

2.2 g of a trans and cis mixture of 1-methyl-1-hydroxy-2-(trimethylsilyl)cyclopropane, prepared in Section 1, was dissolved in 15 mL of dichloromethane, and 1.7 g of triethylamine was added to the resulting solution. The reaction mixture was cooled to 0° C., 1.8 g of methanesulfonylchloride was gradually added thereto and the mixture was vigorously stirred for 1 hour. 5 mL of a saturated NaHCO3 solution was added to the reaction mixture, thereby terminating the reaction. An organic layer was separated, dried over anhydrous magnesium sulfate (MgSO4), and concentrated by low vacuum distillation at a low temperature of less than 30° C. Although it may be used directly without any further purification, the concentrate was finely purified by vacuum distillation (65-70° C./0.1 mmHg). As a result, 2.8 g of 1-methyl-1-(methanesulfonyloxy)-2-(trimethylsilyl)cyclopropane was obtained as a mixture of cis and trans isomers in a ratio of 3 to 4:1. Results of 1H-NMR and 13C-NMR for the major isomer (trans isomer) of the mixture are given below.

Provenance & Evidence