Triethylamine → HCID 267551, compound

To a stirred solution of (1-phenyl-cyclohexyl)-methanol (251) (43.0 g, 225.97 mmol) in dichloromethane (250.0 mL) was added Et3N (63.0 mL, 451.9 mmol), followed by drop-wise addition of mesyl chloride (21.0 mL, 271.16 mmol) at 0° C. and the reaction mixture was stirred at room temperature for 1 h. After completion of the reaction, the reaction mixture was quenched by the addition of water and extracted with dichloromethane. The organic layer was then washed with water and brine and dried over sodium sulfate and concentrated under reduced pressure to get a crude product. It was purified by normal silica gel column chromatography (using 5% ethyl acetate in hexane) to get methanesulfonic acid 1-phenyl-cyclohexylmethyl ester (252) (49.3 g, 81.0%) as a white solid.

1. customAfter completion of the reaction
2. customthe reaction mixture was quenched by the addition of water
3. extractionextracted with dichloromethane
4. washThe organic layer was then washed with water and brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customto get a crude product
8. customIt was purified by normal silica gel column chromatography (using 5% ethyl acetate in hexane)

ORD record

ord-a8fef984ec894256b679a8892df9dcb9

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045486B2