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.

1. customthe cooling bath was removed
2. additiontreated with saturated aqueous sodium bicarbonate solution (25 mL)
3. customThe layers were separated
4. extractionthe aqueous layer extracted with dichloromethane (20 mL)
5. dry with materialThe combined organic layers were dried over magnesium sulfate
6. customthe solvents evaporated under vacuum

ORD record

ord-4c4b634d10a24d28b88d9c8b46642a63

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05866576