N-methyl-2-pyrrolidone → (1-Ethyl)cyclopentyl bromoacetate

Participants

Reaction Steps

Subsequently, a mixed solution containing 14.00 g of 1-ethylcyclopentanol, 220 mL of N-methylpyrrolidone (NMP) and 28.00 g of 1,8-diazabicylco[5,4,0]undec-7-ene (DBU) was cooled in an ice bath, and 61.87 g of bromoacetyl bromide was added dropwise. The mixture was stirred at room temperature for 5 hours, and the reaction solution was cooled in an ice bath. The reaction was then stopped by adding dropwise distilled water, and the reaction solution was diluted with 800 mL of ethyl acetate and washed with 500 mL of distilled water four times. The organic layer was concentrated and purified by column chromatography to obtain 25.43 g of (1-ethyl)cyclopentyl bromoacetate. Also, tert-butyl bromoacetate was obtained in the same manner as above except for changing 1-ethylcyclopentanol to tert-butanol.

Provenance & Evidence