Dimethyl Sulfoxide → tert-Butyl (2-oxoethyl)phenylcarbamate

A solution of oxalyl chloride (0.37 mL) in THF (5.0 mL) was cooled to −78° C., and DMSO (0.39 mL) and THF (2.0 mL) were slowly added dropwise. The reaction mixture was stirred for 5 min, and a solution of the compound (0.50 g) obtained in step 1 in THF (3.0 mL) was added dropwise. The reaction mixture was stirred at −78° C. to −20° C. for 1 hr, and triethylamine (2.0 mL) was added. The reaction mixture was stirred at room temperature for 30 min, poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous ammonium chloride solution and saturated brine, dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (solvent gradient; 5→15% ethyl acetate/hexane) to give the title compound (0.38 g, 77%) as a colorless oil.

1. stirringThe reaction mixture was stirred at −78° C. to −20° C. for 1 hr
2. stirringThe reaction mixture was stirred at room temperature for 30 min
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with saturated aqueous ammonium chloride solution and saturated brine
5. customdried
6. concentrationconcentrated under reduced pressure
7. customThe residue was separated
8. custompurified by silica gel column chromatography (solvent gradient; 5→15% ethyl acetate/hexane)

ORD record

ord-e821a48a966446b9956aba437f3bf25b

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592454B2