3-(Chloromethyl)-5-methyl-1,2-oxazole → HCID 12278252, compound

Sodium methoxide (30% in methanol, 7.46 mmol) was added to 3-chloromethyl-5-methyisoxazole (491 mg, 3.73 mmol) in methanol (4 mL) at room temperature under nitrogen. The reaction mixture was stirred for 15 h at room temperature then heated to reflux for 3 h. After cooling to room temperature the reaction was diluted with ether (75 mL) and washed with saturated aqueous ammonium chloride (15 mL), water (15 mL), and brine (15 mL). The organic layer was dried over magnesium sulfate, filtered, and evaporated to provide 362 mg (76% yield) of 3-methoxymethyl-5-methyl isoxazole as a clear liquid which was used in the next step without further purification: 1H NMR (300 MHz, CDCl3) δ ppm 6.02 (s, 1H), 4.48 (s, 2H), 3.38 (s, 3H), 2.42 (d, J=0.6 Hz, 3H).

1. temperaturethen heated
2. temperatureto reflux for 3 h
3. temperatureAfter cooling to room temperature the reaction
4. washwashed with saturated aqueous ammonium chloride (15 mL), water (15 mL), and brine (15 mL)
5. dry with materialThe organic layer was dried over magnesium sulfate
6. filtrationfiltered
7. customevaporated

ORD record

ord-00fb7bc356904f949cfd7c72417e2acc

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07884107B2