1-Penten-3-Ol → HCID 76576936, compound

Temperature

80 °C

A solution of 1-penten-3-ol (15.0 mL) in N-methyl-2-pyrrolidone (292 mL) was cooled to 0° C. under a nitrogen atmosphere. Sodium hydride (60%, 6.42 g) and bromoacetaldehyde diethyl acetal (31.6 g) were added to the reaction solution at the same temperature, and the mixture was stirred at 80° 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 using 30% ethyl acetate/heptane and concentrated under reduced pressure. Formic acid (100 mL), hydroxylamine hydrochloride (15.2 g) and sodium acetate (24.0 g) were added to the residue, and the mixture was stirred at room temperature for two 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 (4.30 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 using 30% ethyl acetate/heptane
8. concentrationconcentrated under reduced pressure
9. additionFormic acid (100 mL), hydroxylamine hydrochloride (15.2 g) and sodium acetate (24.0 g) were added to the residue
10. stirringthe mixture was stirred at room temperature for two days
11. additionEthyl acetate and a saturated sodium chloride solution were added to the reaction solution
12. customthe organic layer was separated
13. washThe organic layer was washed with saturated aqueous sodium chloride
14. dry with materialdried over anhydrous magnesium sulfate
15. customThe insoluble matter was separated by filtration
16. concentrationthe filtrate was concentrated under reduced pressure
17. customThe residue was purified by silica gel column chromatography

ORD record

ord-34378a8e0a3647abb486c8f7af086fdf

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158620B2