Methyl iodide → ethyl 4-methyl-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

Temperatur

60 °C

In a sealable vessel, potassium carbonate (56 mg, 0.41 mmol) was added to a solution of (±)-ethyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylate (60 mg, 0.29 mmol) and iodomethane (22 □L, 0.35 mmol) in acetone (2 mL). The vessel was sealed and the reaction mixture was stirred at 60° C. for 24 h. The mixture was cooled to ambient temperature, diluted with dichloromethane (60 mL), and the organic layer was extracted with water (10 mL) and half-saturated brine (10 mL). The organic layer was dried over sodium sulfate and concentrated. Purification of the concentrate by flash column chromatography (5% to 10% EtOAc/hexane) afforded the title compound (43 mg, 0.19 mmol). MS m/z: 222 (M+1).

1. customThe vessel was sealed
2. temperatureThe mixture was cooled to ambient temperature
3. extractionthe organic layer was extracted with water (10 mL) and half-saturated brine (10 mL)
4. dry with materialThe organic layer was dried over sodium sulfate
5. concentrationconcentrated
6. customPurification of the
7. concentrationconcentrate by flash column chromatography (5% to 10% EtOAc/hexane)

ORD-Eintrag

ord-ce2e6b8bdf6e4afc9cc84d2f7229f786

Quelldatensatz

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07872009B2