Toluene → (4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one

A mixture of 9.4 grams (0.091 mole) of (S)-2-amino-3-methyl-1-butanol, 36 grams (0.0546 mole) of 85% potassium hydroxide, 175 mL of toluene, and 240 mL of water was stirred rapidly as 140 mL (0.273 mole) of a toluene solution containing 20% phosgene was added dropwise during a 15 minute period. Upon completion of addition, the resulting hot solution was stirred an additional 30 minutes. The reaction mixture was cooled, and the organic and aqueous layers were separated. The organic layer was washed with water and dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure, yielding 15.0 grams of (S)-4-(1-methylethyl)-2-oxazolidinone as a solid. Recrystallization from cyclohexane yielded purer compound, m.p. 71.5°-72.5° C.

1. additionwas added dropwise during a 15 minute period
2. additionUpon completion of addition
3. temperatureThe reaction mixture was cooled
4. customthe organic and aqueous layers were separated
5. washThe organic layer was washed with water
6. dry with materialdried with magnesium sulfate
7. filtrationThe mixture was filtered
8. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-4b8183a3ea5949b0a62bde4a5a275f1e

Source dataset

uspto-grants-1989_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04808762