Hexachloroethane → 2-(4-(2-Chloro-4-methyloxazol-5-yl)phenyl)-2-methylpropanenitrile

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Reaction Steps

To a solution of Example 35C (2.35 g, 10.4 mmol) in THF (50 mL) at −78° C. was added LiHMDS (1.0 M in THF, 11.4 ml, 11.4 mmol) slowly via syringe. The solution was stirred 45 min, and then solid hexachloroethane (3.69 g, 15.6 mmol) was added in one portion. The reaction was allowed to proceed for 16 hr, gradually warming to ambient temperature. The reaction was quenched with half-saturated aq NH4Cl solution, and the product was extracted with Et2O. The combined organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Flash chromatography (Analogix® Intelliflash 280™; 0% to 20% EtOAc/hexanes eluant; SF40-150 g column) yielded 2.52 g (93%) of the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 7.66 (s, 4H), 2.36 (s, 3H), 1.71 (s, 6H). MS (DCI+) m/z 261 (M+H).

Provenance & Evidence