Pyridine → HCID 53758202, compound

Participants

Reaction Steps

A solution of 2,2,2-trichloroethyl chloroformate (1.38 g, 6.5 mmol) in distilled DCM (25 mL) was added dropwise over 0.5 hours to a solution of anhydrous pyridine (1.03 g, 13 mmol) and 191 (1.91 g, 6.5 mmol) in distilled DCM (25 mL) at 0° C. After 6 hours at room temperature, the reaction mixture was diluted with anhydrous DCM (100 mL) and washed with 1 N HCl (2×100 mL), H2O (100 mL), brine (100 mL) and dried over anhydrous MgSO4. Evaporation of the solvent yielded a brown oil which was purified by flash column chromatography (silica gel, EtOAc) to afford the product (192) as a yellow glass (2.13 g, 4.53 mmol, 70%); 1H NMR (270 MHz, CDCl3) δ 7.59 (br s, 1H), 6.56 (s, 1H), 4.78 (br s, 2H), 4.25-4.23 (m, 1H), 3.82-3.79 (m, 3H+1H), 3.69-3.63 (m, 3H+1H), 3.52 (m, 1H), 3.42-3.33 (m, 1H), 2.13-2.06 (m, 3H+1H), 1.88-1.64 (m, 3H); 13C NMR (67.8 MHZ, CDCl3) δ 169.95, 156.82, 156.67, 154.02, 153.34, 131.92, 121.74, 119.33, 103.94, 95.43, 74.42, 66.04, 61.01, 60.60, 60.27, 55.73, 50.46, 28.53, 24.47, 9.13.

Provenance & Evidence