Triethylamine → Methyl 2-(1-[(methanesulfonyloxy)-methyl]cyclopropyl)acetate

Participants

Reaction Conditions

Reaction Steps

8.45 g of crude methyl 2-[1-(hydroxymethyl)cyclopropyl]acetate (compound 14a) was dissolved in 85 ml dry dichloromethane. The pale yellow solution was cooled to 0° C. Then, 7.71 g triethylamine was added and 8.05 g methanesulfonyl chloride was added dropwise over 8 minutes. The yellow suspension was stirred at 0° C. TLC showed that after 10 minutes the reaction was completed. To the reaction mixture, 35 ml water and 20 ml dichloromethane were added. The water layer was washed with 20 ml dichloromethane. The combined organic layers were washed with 30 ml water, dried (Na2SO4) and evaporated to dryness, resulting in a yellow oil. The product was immediately used in the next step (synthesis of methyl 1-(bromomethyl)-cyclopropaneacetate).

Provenance & Evidence