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

Temperature

-78 °C

According to reference (Synthesis 1984, 1048–1050), to a solution of 5-phenyloxazole (1.5 g, 10.3 mmol) in THF:diethyl ether (2:1, 50 mL) at −78° C. is added n-butyl lithium (7.1 mL of 1.6 M solution in hexanes, 11.4 mmol). The reaction is stirred at −78° C. for 30 minutes after which time a solution of N-methyl-2-pyridyl formamide (1.85 mL, 15.5 mmol) in THF (20 mL) is added. The reaction mixture is stirred at −78° C. for 30 min and then at 25° C. for 14 hours. It is quenched by addition of water and extracted with ethyl acetate. The combined organic layers are washed with 10% HCl, saturated sodium bicarbonate and brine before being dried over sodium sulfate and concentrated. The resulting oil is purified by column chromatography (5% ethyl acetate in hexanes) to afford 246 ng of 5-phenyl-1,3-oxazole-2-carbaldehyde.

1. additionis added
2. waitat 25° C. for 14 hours
3. customIt is quenched by addition of water
4. extractionextracted with ethyl acetate
5. washThe combined organic layers are washed with 10% HCl, saturated sodium bicarbonate and brine
6. dry with materialbefore being dried over sodium sulfate
7. concentrationconcentrated
8. customThe resulting oil is purified by column chromatography (5% ethyl acetate in hexanes)

ORD record

ord-70a34fe22c5b4448960fed6448df0c8f

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07041690B2