Chloromethyl Methyl Ether → HCID 67166430, compound

Participants

Reaction Steps

A solution of (2-hydroxy-benzyl)-[3-(2-hydroxy-ethyl)-benzyl]-carbamic acid tert-butyl ester (250 mg) in anhydrous N,N-dimethylformamide (2 mL) was treated with sodium hydride (29 mg of 60% grade reagent) and the mixture stirred under nitrogen for 10 minutes. A solution of chloromethyl methyl ether (62 mg) in anhydrous N,N-dimethylformamide (0.5 mL) was added dropwise followed by stirring at room temperature for 30 minutes. The reaction mixture was partitioned between ethyl acetate and saturated aqueous brine, the organic layer was washed twice with aqueous brine, separated, dried and the solvent evaporated under reduced pressure. The residue was purified on silica eluting with 30% ethyl acetate in isohexane to yield the sub-titled compound (145 mg).

Provenance & Evidence