Diisobutylaluminumhydride → HCID 54176324, compound

Participants

Reaction Steps

A solution of diisobutylaluminum hydride (DIBAL-H, 8.02 mls, 1.54M in toluene) in ether (50 mls) is cooled to -78° C. under N2. A solution of 3-(5-bromo-3-pyridinyl)-2-propenoic acid ethyl ester [see Nishikawa, Y., et al.(1989) J. Med. Chem. 32, 583-593] (1.54 gms, 6.00 mmol) in ether (50 mls) is added. After one hour the dry ice/acetone bath is removed and the mixture is diluted with methylene chloride, dried over Na2SO4, evaporated and chromatographed (1:1 ethyl acetate:hexane followed by 2:1 ethyl acetate:hexane) to yield 1.08 gms of an oil (84%). 1H NMR (DMSO, 300 MHz) δ8.60 (s, 1H), 8.50 (s, 1H), 8.15 (s, 1H), 6.60 (m, 2H), 5.00 (s, 1), and 4.10 (d, J=3.8 Hz, 2H).

Provenance & Evidence