Triethylamine → HCID 54547883, compound

This example illustrates a synthesis of 1-(4,5-Oxohexyl)-3,7-dimethylxanthine (inventive compound no. 1555). To a solution of 4-hexen-1-ol (1.22 g, 12.2 mmol) and methanesulfonyl chloride (1.04 mL, 13.4 mmol) in dichloromethane (15 mL), cooled in an ice bath, was added triethylamine (2.55 mL, 18.3 mmol) dropwise. After 5 minutes, the cooling bath was removed and the mixture stirred for an additional 45 minutes and then treated with saturated aqueous sodium bicarbonate solution (25 mL). The layers were separated and the aqueous layer extracted with dichloromethane (20 mL). The combined organic layers were dried over magnesium sulfate and the solvents evaporated under vacuum, yielding 1-methanesulfonyloxy-4-hexene as a viscous oil.