Acetonitrile → HCID 12518841, compound

Participants

Reaction Steps

To a stirred solution containing 4.36 mL (38.0 mmol) of dimethyl malonate and 2.00 mL (38.0 mmol) of acetonitrile in 20 mL of 1,2-dichloroethane were added 8.90 mL (76.0 mmol) of SnCl4. The reaction mixture was stirred at reflux for 2 h. The reaction mixture was then concentrated under diminished pressure and the residue was dissolved into 100 mL of acetone. Then, 70 mL of satd. aq. sodium carbonate were added and the mixture was stirred for 20 minutes. The mixture was poured into 200 mL of satd. aq. sodium bicarbonate and extracted with two 200-mL portions of DCM. The combined organic solution was washed with a 200-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was recrystallized in ethyl acetate/hexanes to afford the expected product as colorless crystals: yield 3.96 g (60%); mp: 81-82° C.; silica gel TLC Rf 0.5 (1:1 ethyl acetate-hexanes); 1H NMR (CDCl3) δ 2.10 (s, 3H), 3.66 (s, 3H), 3.69 (s, 3H), 5.29 (br s, 1H) and 8.94 (br s, 1H); 13C NMR (CDCl3) δ 22.0, 51.0, 51.6, 92.4, 164.0, 168.7 and 168.9; mass spectrum (APCI), m/z 174.0760 (M+H)+ (C7H12NO4 requires 174.0766).

Provenance & Evidence