Chloromethyl Methyl Ether → HCID 69054868, compound

Participants

Reaction Steps

6-Hydroxy-5,7,8-trimethyl-2,3-dihydro-4H-thiochromen-4-one (2.24 g) was dissolved in anhydrous THF (100 mL) and treated with chloromethyl methyl ether (0.918 mL) and NaH (60% in mineral oil, 483 mg). The resulting reaction mixture was stirred for 2 h turning bright yellow as NaH was added and then gradually becoming pale yellow. The reaction mixture was quenched with a small amount of H2O followed by solvent evaporation and preloading the residue onto SiO2. Column chromatography (SiO2: hexane:EtOAc, 95:5 v/v) yielded 6-methoxymethoxy-5,7,8-trimethyl-2,3-dihydro-4H-thiochromen4-one as a white solid (2.37 g).

Provenance & Evidence