Acetonitrile → HCID 66584535, compound

Participants

Reaction Conditions

Reaction Steps

A solution of CH3CN (48.7 mmol, 2.54 mL) in 10 mL of THF was added dropwise to a solution of nBuLi (48.7 mmol) in 15 mL of THF at −78° C. After stirring for 1 h at −78° C., a solution of methyl tetrahydro-2H-thiopyran-4-carboxylate (24.3 mmol, 3.90 g) in 10 mL of THF was added dropwise and the resulting reaction mixture was stirred at −78° C. for 1 h, then slowly warmed to −40° C. in 2 h. The reaction was quench with 1 N HCl (pH<1). THF was removed and the residue was extracted with EtOAC, washed with brine, dried over Na2SO4, and concentrated. The crude product was purified by a SiO2 column (0-50% EtOAc/Hexanes, Rf=0.45 in 50% EtOAc) to afford compound 3-oxo-3-(tetrahydro-2H-thiopyran-4-yl)propanenitrile (3.60 g, 87.5%) as a light brownish oil. HPLC-MS TR=1.15 min (UV 254 nm, 5 min method); mass calculated for formula C8H11NOS 169.1 observed LCMS m/z 170.1 (M+H).

Provenance & Evidence