Dimethyl Sulfoxide → HCID 60029896, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-6-[2-(1H-imidazol-1-yl)-1-phenylethoxy]-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenone (see example 3, 250 mg, 0.51 mmol), paraformaldehyde (1.5 g) and dimethylsulfoxide (6 mL) was stirred at 130° C. for 24 h. The mixture was diluted with ethanol (10 mL), filtered, concentrated, diluted with water (50 mL) and extracted with ethyl acetate (4×10 mL). The combined extracts were washed with water (3×10 mL), dried (brine, Na2SO4), and concentrated. The residue was purified by dry-flash column chromatography (SiO2, 2.5-22.5% 2-propanol-dichloromethane) to give (S)-6-{2-[2-(hydroxymethyl)-1H-imidazol-1-yl]-1-phenylethoxy}-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenone as a white solid, 161 mg, 61% yield. NMR spectrum was consistent with structure. MS EI: M+* 517.1816 (M+* 517.1797).

Provenance & Evidence