Ethyl Acetate → HCID 15384374, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1,1'-carbonyldiimidazole (178 mg, 1.1 mmol) in pyridine (2.5 mL) at 5° C. under nitrogen was added the product of example 4 (260 mg, 1.1 mmol). The resulting solution was stirred at 5° C. for 15 minutes, diluted with 2.5 mL of DMF and removed from the ice bath. The product of example 8 (375 mg, 1.32 mmol) was added all at once and the reaction mixture stirred at 75°-80° C. for 2 hours. After cooling to room temperature, the resulting solution was diluted EtOAc and washed with 1N HCl, saturated NaHCO3 and dried (MgSO4). Evaporation of the solvent afforded 295 mg (73%) of product (m.p. 177.5°-179° C.). 1H-NMR (300 MHz, CDCl3) δ 1.20-1.30 (m, 6H), 2.05 (m, 1H), 2.53 (m, 2H), 2.83 (m, 1H), 3.83 (m, 2H), 4.15 (q, J=7Hz, 2H), 4.19 (m, 1H), 4.48 (m, 1H), 7.68 (d, J=8Hz, 2H), 7.82 (d, J=8Hz, 2H).

Provenance & Evidence