Aniline → 3-Hydroxymethylheptanoic acid phenylamide

Participants

Reaction Conditions

Reaction Steps

To a solution of aniline (0.36 mL, 4.0 mmol) in toluene (10 mL) was added trimethylaluminum in toluene (2M, 2.5 mL, 5 mmol). After 20 min, a solution of (+/−)-4-butyldihydrofuran-2-one (0.4 g, 4 mmol) in toluene (1 mL) was added and the reaction mixture was refluxed for 3 h. The reaction was cooled to 0° C. and carefully quenched with 1 M HCl (15 mL), and then extracted with dichloromethane (3×15 mL). The combined extractions were dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (silica gel, ethyl acetate/hexanes 3:2) to afford 3-hydroxymethylheptanoic acid phenylamide as a white solid (0.66 g, 70%). MS(ES) m/e 236 [M+H]+.

Provenance & Evidence