3-Acetylbenzonitrile → 317829-69-9

Participants

Reaction Steps

To a solution of (S)-oxazaborolidine (3.44 mmol) in CH2Cl2 (3.5 mL) at −20° C. was added a solution of 3-acetylbenzonitrile (3.47 mmol) in CH2Cl2 (3.5 mL) over a period of approximately 30 minutes. The mixture was then allowed to warm to room temperature for 1 hour then quenched by transferring to a stirred flask of methanol at −20° C. The resultant mixture was concentrated under reduced pressure and the residue taken up in methanol and concentrated twice more and dried overnight under high vacuum. This residue was purified on silica gel chromatography (70:30 hexanes:ethyl acetate) to yield the title compound (373 mg). 1H NMR (500 MHz, CDCl3): δ 7.71 (m, 1H); 7.63 (d, J=7.8 Hz, 1H); 7.58 (m, 1H); 7.48 (t, J=7.7 Hz, 1H); 4.97 (m, 1H); 1.90 (d, J=3.9 Hz,, 1H); 1.53 (d, J=6.6 Hz, 3H).

Provenance & Evidence