Morpholine → 5-Hydroxy-2-(morpholinomethyl)-4H-pyran-4-one

Temperature

80 °C

2-(Bromomethyl)-5-hydroxy-4H-pyran-4-one 21 (5.0 g, 24.4 mmol), morpholine (4.3 mL, 48.8 mmol) and acetonitrile (120 mL) were charged in a 250 ml round-bottomed flask equipped with a magnetic stirrer. The reaction mixture was stirred for 3 h at 80° C. Acetonitrile was evaporated and the residu was extracted with EtOAc (400 mL). The organic layer was washed with water (20 mL), brine (2×20 mL), dried over MgSO4, filtered and evaporated to dryness. Diethyl ether (25 mL) was added and the product was precipitated and filtered to give after drying 5-hydroxy-2-(morpholinomethyl)-4H-pyran-4-one 22 (4.8 g, 72% yield) as a white solid.

1. customequipped with a magnetic stirrer
2. customAcetonitrile was evaporated
3. extractionthe residu was extracted with EtOAc (400 mL)
4. washThe organic layer was washed with water (20 mL), brine (2×20 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated to dryness
8. additionDiethyl ether (25 mL) was added
9. customthe product was precipitated
10. filtrationfiltered
11. customto give

ORD record

ord-756e52f0aa7c4aa68f50ec2817f6305d

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514432B2