Ethyl chloroformate → HCID 22624265, compound

Participants

Reaction Steps

Ethyl chloroformate (0.21 g, 1.95 mM) was added dropwise to a stirred solution of 2-(4-aminobenzoyl)-1-(2-trimethylsilylethoxymethyl)pyrrole (0.5 g. 1.58 mM) in pyridine (5 ml) at 5° C. After 5 minutes the cooling bath was removed and stirring continued for 1.75 hours. The mixture was treated with MeOH (2 ml) and evaporated and the residue partitioned between EtOAc and aqueous sodium bicarbonate solution. The organic layer was washed with water, aqueous citric acid, dried (MgSO4) and evaporated. to give 2-(4-ethoxycarbonylaminobenzoyl)-1-(2-trimethylsilylethoxymethyl)pyrrole as an oil (0.58 g). MS: 389 (MH+). NMR: 0.0 (9H, s); 0.89 (2H, t); 1.38 (3H, t) 3.57 (2H, t); 4.28 (2H, q); 5.8 (2H, s); 6.34 (1H, m); 6.82 (1H, m); 7.50 (1H, m); 7.7 (2H, d); 7.83 (2H, d); 10.1 (1H, br s).

Provenance & Evidence