Water → HCID 69022513, compound

Participants

Reaction Steps

A solution of 3-(4-benzyloxy-phenyl)-4-cyano-1H-pyrrole-2-carboxylic acid ethyl ester (266.70 g, 0.770 mol) in DMSO (2,000 mL) is treated with K2CO3 (117.06 g, 0.847 mol). The resulting solution is allowed to stir at room temperature for several minutes, then treated with iodomethane (58.00 mL, 0.931 mol). The resulting reaction mixture is allowed to stir at room temperature overnight. An additional 0.5 eq of iodomethane (24.00 mL, 0.385 mol) and 0.6 eq of K2CO3 (63.85 g, 0.462 mol) are added to the reaction. The reaction mixture is allowed to stir at room temperature for 2 hours. The reaction mixture is divided into 2 equal portions and each portion is poured into water (2,000 mL) and extracted with EtOAc (3×700 mL each). The combined organics are washed with H2O (2×1000 mL each), dried over anhydrous MgSO4, filtered, then concentrated in vacuo to afford a residue. The residue is slurried in EtOAc (300 mL), then treated with excess hexanes, causing a solid to precipitate. The solid is recovered by vacuum filtration, washing with hexanes, and drying under vacuum filtration to afford the title compound, 3-(4-benzyloxy-phenyl)-4-cyano-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester, (184.73 g, 66% yield) as a light-brown solid: 1H NMR (500 MHz; CDCl3) δ 7.46 (d, 2H), 7.39 (m, 2H), 7.32 (m, 3H), 7.24 (s, 1H), 7.00 (d, 2H), 5.10 (s, 2H), 4.13 (q, 2H), 3.95 (s, 3H), 1.06 (t, 3H); MS(ES): m/z 361.1 (M++H).

Provenance & Evidence