1-Butanol → 3-n-Butoxy-2-hydroxyimino-3-methoxypropionitrile

At room temperature, 5.0 g (60 mmol) of 3-methoxyacrylonitrile, 6.5 g (60 mmol) of n-butyl nitrite and 30 ml of diethyl ether were mixed. Then, 5 ml of the above-mentioned solution was added to a flask having an inner volume of 25 ml and equipped with a stirring device. Under stirring, 1 ml (6 mmol) of a 25.7% by weight hydrogen chloride methanol solution was gradually added dropwise, to generate nitrosyl halide and n-butyl alcohol in the reaction system (the method of the above-mentioned (1)), and the mixture was reacted at room temperature for one hour. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and after adding water to the concentrate, the mixture was extracted with toluene. The organic layer was taken out, washed with a saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, the concentrate was purified by silica gel column chromatography (Filler; Wako gel C-200 (available from Wako Junyaku Co.), Eluent; toluene/ethyl acetate=10/1 (volume ratio)) to obtain 0.06 g (Isolation yield: 4%) of 3,3-di-n-butoxy-2-hydroxyiminopropionitrile as colorless oily product, 0.21 g (Isolation yield: 19%) of 3-n-butoxy-2-hydroxyimino-3-methoxypropionitrile as colorless oily product and 0.14 g of 3,3-dimethoxy-2-hydroxyiminopropionitrile (Isolation yield: 16%) as white solid.

1. customequipped with a stirring device
2. customwas reacted at room temperature for one hour
3. customAfter completion of the reaction
4. concentrationthe reaction mixture was concentrated under reduced pressure
5. additionafter adding water to the concentrate
6. extractionthe mixture was extracted with toluene
7. washwashed with a saturated aqueous sodium hydrogen carbonate solution
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationAfter filtration
10. concentrationthe filtrate was concentrated under reduced pressure
11. customthe concentrate was purified by silica gel column chromatography (Filler; Wako gel C-200 (available from Wako Junyaku Co.), Eluent; toluene/ethyl acetate=10/1 (volume ratio))

ORD record

ord-068b40a476df4c02a9fe93236e64f8ee

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07227032B2