Water → HCID 86746501, compound

Participants

Reaction Conditions

Reaction Steps

16.4 g (52.5 mmol) of 5-dithiophenylmethyl-1-methylimidazole are dissolved in 240 ml of tetrahydrofuran and cooled to -78° C. 52.5 mmol of n-BuLi in 32 ml of hexane are added dropwise to this. After 30 minutes at -78° C., 4.9 ml (69.8 mmol) of γ-crotonolactone are added and, after a further 1.5 hours, 250 ml of water are added dropwise while cooling in dry ice, and the mixture is allowed to warm to room temperature. It is then washed with ethyl acetate, acidified with glacial acetic acid and again extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and concentrated in vacuo. The residue obtained in this way (13.8 g) is chromatographed on silica gel with dichloromethane/methanol (9:1). 6.6 g (16.6 mmol, 32%) of 3-(1-methylimidazol-5-yl-(dithiophenyl)methylbutyrolactone are obtained as a white powder of melting point 80° C.

Provenance & Evidence