N-Methyl-N-(pyridine-2-yl)formamide → 5-Phenyl-1,3-oxazole-2-carbaldehyde

Temperature

-78 °C

A solution of 5-phenyloxazole (0.192 g) in 2:1 tetrahydrofuran/diethyl ether (7 mL) was cooled to −78° C., and treated with n-butyl lithium (0.582 mL) dropwise under Argon. The mixture was stirred for 30 minutes at −78° C., at this time a solution of N-methyl-N-(pyridin-2-yl) formamide (0.270 g) in tetrahydrofuran (2.6 mL) was added dropwise to the solution. After stirring at −78° C. for 30 minutes, the mixture was allowed to warm up to room temperature and stirring continued overnight. The mixture was quenched by the addition of water and extracted with ethyl acetate. The combined extracts were washed with 10% hydrochloric acid, saturated aqueous solution of sodium bicarbonate and brine, dried and concentrated in vacuo and purified by column chromatography on silica gel (10-50% ethyl acetate in hexane) to provide the title compound (0.016 g) with the following physical data.

1. additionwas added dropwise to the solution
2. temperatureto warm up to room temperature
3. stirringstirring continued overnight
4. customThe mixture was quenched by the addition of water
5. extractionextracted with ethyl acetate
6. washThe combined extracts were washed with 10% hydrochloric acid, saturated aqueous solution of sodium bicarbonate and brine
7. customdried
8. concentrationconcentrated in vacuo
9. custompurified by column chromatography on silica gel (10-50% ethyl acetate in hexane)

ORD record

ord-f2d9d2c5a26f4869a16fcf4cd50ea6cd

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809538B2