Tetrahydrofuran → HCID 13093107, compound

To a solution of 4-(benzyloxy)butanoic acid (25.2 g) and DMF (5 drops) in THF (200 ml) was added dropwise oxalyl chloride (25 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 3 hr, and the solvent and volatile component were evaporated. A solution of the residue in dichloromethane (50 ml) was added dropwise to a solution of Meldrum's acid (15.6 g) and pyridine (18 ml) in dichloromethane (100 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 11 hr, washed with 0.5M hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated. A solution of the residue in methanol (500 ml) was stirred with heating under reflux for 9 hr. After cooling to room temperature, the solvent was evaporated. The residue was purified by silica gel column (hexane/ethyl acetate=5/1) to give the title compound as a pale-yellow liquid (14.37 g, 55%).

1. temperaturecooling
2. customthe solvent and volatile component were evaporated
3. additionA solution of the residue in dichloromethane (50 ml) was added dropwise to a solution of Meldrum's acid (15.6 g) and pyridine (18 ml) in dichloromethane (100 ml) under ice-
4. temperaturecooling
5. stirringThe reaction mixture was stirred at room temperature for 11 hr
6. washwashed with 0.5M hydrochloric acid and saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. customthe solvent was evaporated
9. stirringA solution of the residue in methanol (500 ml) was stirred
10. temperaturewith heating
11. temperatureunder reflux for 9 hr
12. temperatureAfter cooling to room temperature
13. customthe solvent was evaporated
14. customThe residue was purified by silica gel column (hexane/ethyl acetate=5/1)

ORD record

ord-fe936d846cb04e95b21f13cdc851190a

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803822B2