Acetone → HCID 15885495, compound

Participants

Reaction Steps

A solution of 1-(10-undecenyl)-3,7-dimethylxanthine (4.3 g, 13 mmol), prepared above, 4-methylmorpholine-N-oxide (1.942 g, 16.6 mmol) and potassium osmate dihydrate (9.5 mg, 0.026 mmol) in acetone (45 ml) and water (10 ml) was stirred for 6 hours. A solution of 20% aqueous sodium sulphite (12 ml) was added and stirred for 30 minutes. The reaction mixture was extracted with four 100 ml aliquots of 25% ethanol/dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate. Evaporating the solvent under reduced pressure left a residue, which upon subsequent purification by flash chromatography over silica gel using a methanol (5%)/dichloromethane eluant produced 3.6 g of 1-(10, 11-dihydroxyundecanyl)-3,7-dimethylxanthine (76% yield).

Provenance & Evidence