3-Buten-2-ol → HCID 76576789, compound

Temperature

60 °C

A solution of 3-buten-2-ol (5.00 g) in N-methyl-2-pyrrolidone (70.0 mL) was cooled to 0° C. under a nitrogen atmosphere. Sodium hydride (600, 3.33 g) and bromoacetaldehyde diethyl acetal (15.0 g) were added to the reaction solution at the same temperature, and the mixture was stirred at 60° C. for 30 minutes. A saturated ammonium chloride solution was added to the reaction solution at 0° C., followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The insoluble matter was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in heptane. The solution was filtered through silica gel and concentrated under reduced pressure. Formic acid (30.0 mL) and water (10.0 mL) were added to the residue, and the mixture was stirred at room temperature for 30 minutes. Hydroxylamine hydrochloride (5.78 g) and sodium acetate (11.4 g) were added to the reaction solution at the same temperature, and the mixture was stirred at room temperature for five days. Ethyl acetate and a saturated sodium chloride solution were added to the reaction solution, and the organic layer was separated. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The insoluble matter was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (2.29 g).

1. extractionfollowed by extraction with ethyl acetate
2. washThe organic layer was washed with saturated sodium bicarbonate and saturated aqueous sodium chloride
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe insoluble matter was separated by filtration
5. concentrationthe filtrate was concentrated under reduced pressure
6. dissolutionThe residue was dissolved in heptane
7. filtrationThe solution was filtered through silica gel
8. concentrationconcentrated under reduced pressure
9. additionFormic acid (30.0 mL) and water (10.0 mL) were added to the residue
10. stirringthe mixture was stirred at room temperature for 30 minutes
11. additionHydroxylamine hydrochloride (5.78 g) and sodium acetate (11.4 g) were added to the reaction solution at the same temperature
12. stirringthe mixture was stirred at room temperature for five days
13. additionEthyl acetate and a saturated sodium chloride solution were added to the reaction solution
14. customthe organic layer was separated
15. washThe organic layer was washed with saturated aqueous sodium chloride
16. dry with materialdried over anhydrous magnesium sulfate
17. customThe insoluble matter was separated by filtration
18. concentrationthe filtrate was concentrated under reduced pressure
19. customThe residue was purified by silica gel column chromatography

ORD record

ord-4c97a353e1ac48cc90712e7a328ec93d

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946211B2