Acetonitrile → Benzoylacetonitrile

Participants

Reaction Steps

To 50 mL of THF at −78° C. was added n-BuLi (58.8 mL, 147.0 mmol, 2.5 M in hexanes). After the reaction temperature equilibrated (˜15 min), a solution of acetonitrile (7.7 mL, 147.0 mmol in 100 mL of THF) was added dropwise via an addition funnel over a 20 min period. The resulting milky-white slurry was allowed to stir for 1 hr before a solution of methyl benzoate (10.0 g, 73.5 mmol in 20 mL of THF) was added down the inside of the flask over a 15 min period. After 1 hr, the reaction was warmed to −45° C. (acetonitrile/CO2) and allowed to stir for 2 hr. The reaction was quenched cold by the dropwise addition of 2 N HCl, pH=7 and then diluted with EtOAc. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound (quantitative yield) as a colorless solid that was used without further purification. LRMS m/z (APCl) 144 (M−1); 500 MHz 1H NMR (CDCl3) δ 7.92 (dd, J=8.4, 1.2 Hz, 2H), 7.66-7.64 (m, 1H), 7.55-7.50 (m, 2H), 4.09 (s, 2H).

Provenance & Evidence