Methanol → 2-(2-Benzyloxy-3-pyridyl)acetonitrile

Temperature

-78 °C

To a mixture of potassium t-butoxide (4.52 g) and dimethoxyethane (20 mL) was added a solution (20 mL) of toluenesulfonylmethylisocyanide (4.12 g) in dimethoxyethane at −78° C. Further, a solution (20 mL) of 2-(benzyloxy)nicotinaldehyde (4.12 g) in dimethoxyethane was added to the reaction mixture. The reaction mixture was stirred at −78° C. for 1 hr. Methanol (20 mL) was added to the reaction mixture at room temperature and the mixture was heated under reflux for 30 min. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give 2-(2-benzyloxy-3-pyridyl)acetonitrile as an oil from a fraction eluted with ethyl acetate-hexane (1:8, v/v).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 30 min
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated

ORD record

ord-41350c36b0494a45809af0e215b40030

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07238716B2