Methanol → HCID 10488349, compound

Temperature

-78 °C

To a stirred solution of ethyl (2E)-3-(2,4-dichlorophenyl)acrylate (11.3 g, 46 mmol) in tetrahydrofuran at −10° C. was added diisobutylaluminium hydride (1.0 M in toluene, 100 ml, 0.11 mol) dropwise. After addition was complete, the reaction was cooled to −78° C. and methanol (40 ml) added dropwise. Ammonium chloride (sat. aq., 70 ml) was then added and the reaction allowed to warm to 0° C. After 15 min at 0° C. the reaction was allowed to warm to room temperature and stirred for 1 h. The mixture was then filtered through a pad of hyflo supercel (washing well with ethyl acetate) and the concentrated to give the title compound (7.8 g) as pale yellow crystals. 1H NMR δ (ppm)(CDCl3): 7.44 (1 H, d, J=8.4 Hz), 7.36 (1 H, d, J=2.0 Hz), 7.19 (1 H, dd, J=2.0, 8.5 Hz), 6.93 (1 H, d, J=15.8 Hz), 6.36-6.28 (1 H, m), 4.35 (2 H, d, J=5.4 Hz), 1.84 (1 H, s).

1. additionAfter addition
2. temperatureto warm to 0° C
3. temperatureto warm to room temperature
4. filtrationThe mixture was then filtered through a pad of hyflo supercel (
5. washwashing well with ethyl acetate) and the
6. concentrationconcentrated

ORD record

ord-917ece0eec46449d9168e8c7c7e43f66

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07728022B2