Methyl (E)-3-(2-quinolinyl)-2-propenoate → 3-(Quinolin-2-yl)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

Methyl(2E)-3-(quinolin-2-yl)prop-2-enoate G5 (2.37 g, 11.1 mmol) dissolved in 100 mL THF was cooled to 0° C. and treated with a 1M solution of LAH in THF (33.3 mL, 33.3 mmol) dropwise over 5 minutes. The reaction was allowed to warm to room temperature and stir overnight. The reaction was then carefully quenched with 1.3 mL of water, 1.3 mL of 15% NaOH, and 3.9 mL of water, Solid Na2SO4 was added and the slurry was stirred for 2 hours, filtered and concentrated by rotary evaporation. The residue was purified by silica gel flash column chromatography (EtOAc/hexanes gradient) to provide 575 mg (27%) of G6 as a brown oil. MS (Electrospray): m/z 188.2 (MH+).

Provenance & Evidence