Methyl iodide → HCID 90389298, compound

Participants

Reaction Steps

To a solution of (5-(chloromethyl)-4,5-dihydroisoxazol-3-yl)methanol (6c rac, 2.2 g, 14.71 mmol) in THF (40 mL) was added sodium hydride (60% dispersion in mineral oil, 0.372 ml, 17.65 mmol). The resulting mixture was stirred for 15 min followed by dropwise addition of methyl iodide (1.005 ml, 16.18 mmol). After 15 min, the reaction mixture was carefully quenched with aqueous saturated ammoniumchloride solution and diluted with water. The phases were separated and the aqueous phase was extracted with Et2O. The combined organic layers were dried over Na2SO4 and the filtrate was concentrated under reduced pressure to afford the title compound as a pale yellow oil. The oil was dissolved in THF (20 mL) and the solution was cooled 0° C. A solution of potassium tert-butoxide (1M in THF, 17.65 ml, 17.65 mmol) was added dropwise and the reaction mixture was stirred for 30 min at 0° C. The mixture was quenched with aqueous saturated ammoniumchloride solution, the phases were separated and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and the filtrate was concentrated under reduced pressure to afford the title compound as an orange oil as MS m/z=128.1[M+H]+. Calculated for C6H9NO2: 127.06.

Provenance & Evidence