Tert-Butyl isocyanide → 4-Methoxyoxane-4-carbonitrile

Temperature

-78 °C

Under an argon atmosphere, 4,4-dimethoxytetrahydropyran (4.39 g, 30.0 mmol) was dissolved in dichloromethane (60 mL), and tert-butyl isocyanide (3.73 mL, 33.0 mmol) and titanium tetrachloride (3.95 mL, 36.8 mmol) were added thereto at −78° C., and then, the mixture was stirred overnight at room temperature. To the mixture, an aqueous sodium hydrogen carbonate solution was added, and the mixture was filtered through Celite, and then, the filtrate was extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20) to give 4-methoxytetrahydropyran-4-carbonitrile (3.30 g, 23.4 mmol, yield: 78%).

1. filtrationthe mixture was filtered through Celite
2. extractionthe filtrate was extracted with chloroform
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customthe solvent was evaporated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20)

ORD record

ord-48983d2434924313ac37912bcec33dbf

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273738B2