Acetonitrile → HCID 90406336, compound

Participants

Reaction Steps

The solution of CH3CN (0.37 g, 8.9 mmol) in THF (40 mL) was added to n-BuLi (1.6 M in hexanes, 0.58 g, 8.9 mmol) at −78° C. and the reaction mixture was stirred for 30 min. Solution of ester (12) (1.5 g, 5.9 mmol) in THF (10 mL) was added to the reaction mixture and the resulting solution was further stirred for 30 min. The reaction mixture was quenched by addition of aq.NH4Cl (200 mL) and extracted with EtOAc (100 mL). Drying over anhydrous Na2SO4 and concentration under reduced pressure gave 3-oxo-3-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)propanenitrile (13). Yield (1.5 g, 96%); 1H NMR (400 MHz, DMSO-d6) δ 7.43-7.37 (m, 3H), 7.26-7.21 (m, 1H), 4.75 (bs, 2H), 3.89-3.83 (m, 4H), 3.32 (t, J=11.6 Hz, 2H), 2.03-1.98 (m, 1H), 1.69-1.66 (m, 2H), 1.38-1.28 (m, 2H).

Provenance & Evidence