2(3H)-Benzoxazolone → 2-Benzoxazolinone, 3-methyl-

Temperature

0 °C

NaH (280 mg, 7.00 mmol) was added to a chilled (0° C.) solution of benzo[d]oxazol-2(3H)-one (650 mg, 4.81 mmol) in tetrahydrofuran (20 mL). After 0.5 hours, methyl iodide (1.03 g, 7.25 mmol) was added dropwise with stirring, maintaining a temperature of 0° C. The resulting solution was then stirred for 6 hours at room temperature. The reaction mixture was then quenched by the addition of ethanol (10 mL), and the mixture was concentrated. Water (50 mL) was then added and the resulting solution was extracted with dichloromethane (3×20 mL). The organic layers were combined, dried (Na2SO4), filtered and concentrated to afford 0.62 g (82%) of 3-methylbenzo[d]oxazol-2(3H)-one as a light red solid.

1. stirringThe resulting solution was then stirred for 6 hours at room temperature
2. customThe reaction mixture was then quenched by the addition of ethanol (10 mL)
3. concentrationthe mixture was concentrated
4. additionWater (50 mL) was then added
5. extractionthe resulting solution was extracted with dichloromethane (3×20 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-e598621ab45f45fea6bd714bf6d5c552

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696229B2