Chloromethyl Methyl Ether → HCID 67003828, compound

Participants

Reaction Steps

To a cold (0° C.) suspension of sodium hydride (1.07 g, 44.4 mmol) in N,N-dimethylformamide (50 mL) was added a solution of 1-(thiazol-2-yl)cyclobutanol (Example 1A) (5.3 g, 34.1 mmol) in N,N-dimethylformamide (18 mL). After 0.5 hours, chloro(methoxy)methane (3.89 ml, 51.2 mmol) was added, and the reaction was stirred for 16 hours. The reaction was quenched by the addition of ether and water. The layers were separated, and the aqueous layer was extracted with additional ether. The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 0 to 50% ethyl acetate in hexane, to give the title compound. MS ESI(+) m/z 200 [M+H]+.

Provenance & Evidence