Toluene → HCID 11144022, compound

Participants

Reaction Steps

A solution of 2-(4-benzyloxyphenyl)-1-ethylindolizine (6.55 g, 20 mmol) and methylpropiolate (10.4 g, 124 mmol) in 250 ml of dry toluene was heated to 100° C. under nitrogen atmosphere and stirred for 21/2 hour. The mixture was cooled to room temperature and 2,3-dichloro-5,6-dicyano-1,4-benzoequinone (1.84 g, 8.1 mmol) was added and stirring was continued for 1 our. The mixture was filtered through celite and the solvent removed. The crude product was purified by column chromatography over silica gel 60, using 20% of diethyl ether in hexane as the eluent to afford 4.82 g (58%) of methyl 3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1-carboxylate. M.p. 129-131° C. MS(SP): m/z 409 (M+). 1H-NMR (CDCl3, 200 MHz) δ: 1.47 (t, 3H); 3.22 (q, 2H); 4.01 (s, 3H); 5.16 (s, 2H); 7.15 (d, 2H); 7.32-7.52 (m, 5H); 7.72 (d, 2H); 7.75-7.90 (m, 2H); 8.03 (s, 1H); 8.33 (dd, 1H). Analysis: Calculated for C27H23N1O3 : C, 79.20; H, 5.66; N, 3.42%; Found: C, 79.10; H, 5.50; N, 3.20%.

Provenance & Evidence