Toluene → (E)-3-(3,4-Difluorophenyl)acrylaldehyde

Temperature

-78 °C

(E)-3-(3,4-Difluorophenyl)-N-methoxy-N-methyl-prop-2-enamide (100 mg, 0.440 mmol) is dissolved in dry tetrahydrofuran under inert atmosphere and the resulting solution is cooled to −78° C. A solution of diisobutylaluminum hydride in toluene (1M, 1100 μl, 1.100 mmol) is slowly added and the resulting mixture is stirred for 1 h at −78° C. The reaction is allowed to warm up to room temperature and is stirred for 1 h at this temperature. The reaction mixture is concentrated under reduced pressure and the crude product is purified by flash column chromatography on silica gel (heptane/ethyl acetate 0 to 50% as eluent) to afford the desired product as white oil (56 mg, 0.333 mmol, 76% yield).

1. temperatureto warm up to room temperature
2. stirringis stirred for 1 h at this temperature
3. concentrationThe reaction mixture is concentrated under reduced pressure
4. customthe crude product is purified by flash column chromatography on silica gel (heptane/ethyl acetate 0 to 50% as eluent)

ORD record

ord-192a428fd3f0476fb46a98475f13306c

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096599B2