Tetrahydrofuran → HCID 67200023, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxazole (0.5 mL, 7.6 mmol) in 50 mL of THF at −78° C. under nitrogen atmosphere n-BuLi (1.6 M in hexanes, 4.7 mL, 7.60 mmol) was added. After stirring 20 min ZnCl2 (2.071 g, 15.2 mmol) was added and the mixture warmed to 0° C. and stirred 45 min. Then CuI (1.45 g, 7.6 mmol) was added and, after 20 min, a solution of 2-(chlorocarbonyl)phenylpropionitrile (15.2 mmol), prepared as previously described, in 10 mL of THF was added by dripping. The mixture was left stirring 2 h. The organic phase was diluted with EtOAc and washed sequentially with a saturated solution of NaHCO3 (2×50 mL) and brine (50 mL). After drying over Na2SO4 and solvent evaporation under reduced pressure a residue was obtained that, after flash chromatography, afforded 2-[3-(oxazole-2-carbonyl)phenyl]propionitrile as pale yellow oil (1.27 g, 5.63 mmol). Yield 74%.

Provenance & Evidence