Triacetoxyperiodinane → Methyl 3-[5-formyl-imidazol-1-yl]-3-(4-cyano-phenyl)-propionate

Participants

Reaction Steps

To a solution of the title B compound, methyl 3-[5-(hydroxymethyl)-imidazol-1-yl]-3-(4-cyano-phenyl)-propionate (0.60 g, 2.11 mmol) in DCM (7.0 mL) is added Dess-Martin periodinane (15% wt solution, 7.0 mL, 3.2 mmol) and the reaction is stirred for 3 h. The reaction mixture is partitioned between EtOAc and sodium bicarbonate-sodium thiosulfate. The combined organic phases are washed with brine and dried (anhydrous sodium sulfate) and concentrated. The residue is subjected to flash chromatography (silica) eluting with EtOAc:MeOH (9:1) to give methyl 3-[5-formyl-imidazol-1-yl]-3-(4-cyano-phenyl)-propionate as an oil: 1H-NMR (CDCl3) δ 9.68 (1H, s), 8.00 (1H, s), 7.87 (1H, s), 7.65 (2H, d, J=8.5), 7.37 (2H, d, J=8.5), 6.63 (1H, m), 3.66 (3H, s), 3.43 (1H, dd, J=16.5, 8.5), 3.30 (1H, dd, J=16.5, 6.6); 13C-NMR (CDCl3) δ 178.9, 169.2, 144.9, 143.0, 141.8, 132.7, 130.8, 127.4, 118.0, 112.5, 56.5, 52.4, 39.0; e/z (ES) 284 (M+1, 100%).

Provenance & Evidence