Dichloromethane → 3-(Ethoxycarbonyl)-4-(1,5-dimethoxypent-3-yl)pyrrole

Participants

Reaction Steps

A solution of 24 (3.00 g, 13.03 mmol) and TosMIC (2.54 g, 13.02 mmol) in DMSO/Et2O (1:2, 25 mL) was added via cannula to a vigorously stirred suspension of NaH (649 mg, 27.04 mmol) in Et2O (11.3 mL) under argon. Stirring was continued for 3 h. Brine and CH2Cl2 were added in small portions. The aqueous layer was extracted with CH2Cl2. The organic extract was washed with brine. The solvent was removed at reduced pressure. The oily residue was chromatographed [silica, CH2Cl2/ethyl acetate (9:1)] to yield a pale yellow oil (2.59 g, 74%): 1H NMR δ 1.32 (t, J=7.2 Hz, 3H), 1.88-1.95 (m, 4H), 3.26-3.33 (m, 10H), 4.24 (q, J=7.2 Hz, 2H), 6.54 (s, 1H), 7.37 (s, 1H), 8.74 (br, 1H); 13C NMR δ 14.59, 30.35, 36.04, 58.50, 59.47, 71.65, 114.69, 116.66, 124.92, 129.05, 165.28; FAB-MS obsd 270.1703, calcd 270.1705 [(M+H)+, M=C14H23NO4].

Provenance & Evidence