N,N,N',N'-Tetramethylazodicarboxamide → HCID 68537736, compound

Participants

Reaction Steps

To a solution of 5-(diphenylmethyl)-1-(2-hydroxyethyl)pyridin-2(1H)-one (300 mg) in toluene (4.0 mL) were added 1,1′-azobis(N,N-dimethylformamide) (203 mg) and tributylphosphine (291 μL) at ambient temperature. And then to the mixture was added a solution of ethyl 4-[(3-hydroxyphenyl)sulfanyl]butanoate (378 mg) in toluene (2.0 mL) at 0° C. After stirring at ambient temperature for an hour, the reaction mixture was diluted with EtOAc (10 mL). The mixture was washed with water (10 mL) and brine (10 mL). The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo to give crude oil. The oil was purified by silica gel column chromatography(n-hexane:EtOAc=4:1-1:1) to give ethyl 4-[(3-{2-[5-(diphenylmethyl)-2-oxopyridin-1(2H)-yl]ethoxy}phenyl)sulfanyl]butanoate (436 mg) as a colorless oil.

Provenance & Evidence