Water → 1-(16-Heptadecenyl)-3,7-dimethylxanthine

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium theobromine (2.02 g, 10.0 mmol) in dimethylsulfoxide/tetrahydrofuran (2:1, 30 ml) was added 16-heptadecenyl chloride and the reaction stirred for 16 hours at 60° C. The mixture was then poured into water (75 ml) and extracted with ethyl acetate (3×75 ml). The organic portions were combined, dried over magnesium sulfate and the solvent evaporated, leaving a cream-colored solid residue. Recrystallization of the residue from hot hexane resulted in 2.31 g of 1-(16-Heptadecenyl)-3,7-dimethylxanthine as a white solid (85% yield).

Provenance & Evidence