Toluene → [2-(2,5-Dimethoxy-phenyl)-cyclopentyl]-acetaldehyde

Participants

Reaction Conditions

Reaction Steps

Dissolve [2-(2,5-dimethoxy-phenyl)-cyclopentyl]-acetonitrile (3.9 g, 16 mmol) in ether (85 ml), cool to −10° C., add diisobutylaluminum hydride 1.5M in toluene (19 ml, 29 mmol), and stir at −10° C. for 1 hour. Quench with 1N hydrochloric acid, and add ethyl acetate. Separate layers, wash organic with brine, dry, and concentrate to give the title compound (3 g, 76%): 1H NMR (CDCl3) δ 9.50-9.49 (m, 1H), 6.77-6.69 (m, 3H), 3.77 (s, 3H), 3.76 (s, 3H), 3.58-3.54 (m, 1H), 2.88-2.83 (m, 1H), 2.08-1.87 (m, 5H), 1.74-1.65 (m, 2H), 1.44-1.39 (m, 1H).

Provenance & Evidence