Chloroacetonitrile → 1,6-Dioxaspiro[2.5]octane-2-carbonitrile

Tetrahydro-4H-pyran-4-one (2.50 g, 25.0 mmol) and chloroacetonitrile (1.58 mL, 25.0 mmol) were dissolved in tert-butanol (5.0 mL). To this, a tert-butanol solution (25 mL) of potassium tert-butoxide (2.81 g, 25.0 mmol) was added dropwise and the mixture was stirred at room temperature for 1 hour. The reaction was stopped by successive addition of ice and a 1 mol/L aqueous hydrogen chloride solution (30 mL) to the reaction mixture, and extraction with ether was performed, followed by washing with brine and drying over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3) to give 1,6-dioxaspiro[2.5]octane-2-carbonitrile (3.14 g, yield: 90%).

1. additionThe reaction was stopped by successive addition of ice
2. extractiona 1 mol/L aqueous hydrogen chloride solution (30 mL) to the reaction mixture, and extraction with ether
3. washby washing with brine
4. dry with materialdrying over anhydrous magnesium sulfate
5. customThe solvent was evaporated off under reduced pressure
6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3)

ORD record

ord-4d4d74bc40904027b45c61e640248621

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673908B2