Boron trifluoride etherate → 850991-77-4

Participants

Reaction Steps

To a stirred solution of ethyl N-(hydroxymethyl)cyclohex-3-en-1-ylmethylcarbamate (213 mg, 1.00 mmol) in 15 mL of dichloromethane, cooled in an ice bath, was added drop-wise boron trifluoride etherate (0.19 mL, 1.5 mmol). The initially cloudy reaction mixture slowly cleared. After it had become homogenous, it was warmed to ambient temperature and stirred for 1.5 h. The reaction was quenched by sequential addition of 5 mL of water and 5 mL of 10% KOH solution. The mixture was extracted with dichloromethane (2×20 mL), and the combined extracts were washed with brine (25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was column chromatographed on silica gel with 2:1 hexane/ethyl acetate to give the product as a colorless oil (145 mg, 74%).

Provenance & Evidence