Boron trifluoride etherate → 850991-77-4

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%).

1. customThe initially cloudy reaction mixture
2. customThe reaction was quenched by sequential addition of 5 mL of water and 5 mL of 10% KOH solution
3. extractionThe mixture was extracted with dichloromethane (2×20 mL)
4. washthe combined extracts were washed with brine (25 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customchromatographed on silica gel with 2:1 hexane/ethyl acetate

ORD record

ord-296287610d6a46e890ed30cd6ade912a

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402592B2