Benzonitrile → HCID 68648017, compound

Participants

Reaction Steps

2-(3-Methyl-5-isoxazolyl)-1-phenyl-1-ethanone. To a solution of 8.73 g (90 mmol) of 3,5-dimethylisoxazole in 100 mL of THF at −70° C. under N2 was added dropwise a 1.55 M solution of nBuLi in hexanes (56.4 mL, 87 mmol). After stirring cold for 30 m, a solution of 10.3 g (100 mmol) of benzonitrile in 50 mL of THF was added dropwise. The reaction was allowed to warm to rt and stirred overnight. The solvent was removed in vacuo and the residue was partitioned between EtOAc and water. The organic layer was separated, washed with an aq. 1N HCl solution, dried (Na2SO4), filtered and conc. to dryness. Purification by silica gel chromatography (1:1 EtOAc/hexanes) followed by recrystallization gave the desired product as colorless crystals, mp 75-77° C. (25% yield; lit, Hicks, M. J. and Tong, Y. C., U.S. Pat. No. 5,338,856, Aug. 16, 1994, mp 73-74° C.). 1H NMR (CDCl3, 400 MHz) δ 8.00 (d, 2H), 7.60 (m, 1H), 7.50 (d, 2H), 6.15 (s, 1H), 4.40 (s, 2H), 2.30 (s, 3H); TOF MS ES+ m/z 202 (MH+).

Provenance & Evidence