Dimethyl Sulfide → {1-[4-(8-Formyl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of {1-[4-(4-oxo-2-phenyl-8-vinyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester in MeOH (1 mL) and DCM (4 mL) was cooled with stirring to −78° C. Ozone was bubbled through the reaction mixture for 75 min with stirring, followed by air for 5 min with stirring. Dimethylsulfide (0.027 ml, 0.366 mmol) was added and the resultant mixture was allowed to warm to RT and stirred for 2 h. The solvent was removed by bubbling nitrogen through the reaction mixture. The residue was dissolved in EtOAc and washed with brine. The organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a gum (81 mg, 90%). LCMS (Method G): RT=4.24 min, [M+H]+=496.

Provenance & Evidence