Sodium hydride → HCID 18919259, compound

Participants

Reaction Conditions

Reaction Steps

Under argon gas, diethyl 1H-pyrrole-2,3-dicarboxylate (4.79 g) was dissolved in DME (100 ml) and the solution was cooled to 0° C. Then, sodium hydride (990 mg) was added and the mixture was stirred at room temperature for 0.5 hour, after which it was cooled to 0° C. again. To this reaction mixtrue was added 4-(4-chlorobenzoyl)benzyl bromide (8.53 g) and the mixture was stirred at room temperature for 14 hours. This reaction mixture was diluted with water and extracted with ethyl acetate (500 ml) and the organic layer was washed with NaHCO3 /H2O (300 ml) twice and saturated aqueous NaCl solution (100 ml) once, and dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (stationary phase 250 g; hexane: ethyl acetate=6:1→1:1) to provide 9.56 g (yield 96%) of the title compound. 1H-NMR (CDCl3) δ: 1.26(3H,t,J=7.1Hz), 1.35(3H,t,J=7.0Hz), 4.26(2H,q,J=7.1Hz), 4.30(2H,q,J=7.1 Hz),5.49(2H,s), 6.57(1H,d,J=3.OHz), 6.88(1H,d,J=3.2Hz), 7.19(2H,d,J=8.4Hz), 7.45(2H,d,J=8.6Hz), 7.72(4H,d,J=8.8Hz).

Provenance & Evidence