Methanol → Methyl[1-(3-bromopropyl)cyclopropyl]acetate

Participants

Reaction Steps

Under argon and at 0° C., 3.4 ml (3.4 mmol) of borane/THF complex solution (1 M in THF) were added dropwise to 1542 mg (10 mmol) of methyl [1-(prop-2-en-1-yl)cyclopropyl]acetate in 10 ml of anhydrous THF. After 30 min at 0° C., the reaction was stirred at RT for a further 30 min, and 22 μl (0.54 mmol) of methanol were then added. At −5° C., 0.62 ml (12 mmol) of bromine and 2971 mg (16.5 mmol) of sodium methoxide solution (30% in methanol) were then successively added dropwise to the reaction mixture. Once the reaction had reached room temperature, 10 ml of saturated sodium bicarbonate solution were added, the organic phase was separated off and the aqueous phase was extracted three more times with tert-butyl methyl ether. The combined organic phases were washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure gave 683 mg (2.9 mmol, 29% of theory) of the title compound as a yellow oil.

Provenance & Evidence