Triethylsilane → HCID 53246150, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-(3-(4-fluorophenyl)-5-ethyl-2-phenyl-1H-pyrrol-1-yl)acetate (0.8 g, 2.371 mmol) was dissolved in 10 mL DCM and cooled to −78° C. Trimethylsilyl trifluoromethylsulfonate (0.964 ml, 5.34 mmol) was then added, followed by triethylsilane (1.136 ml, 7.11 mmol). The reaction mixture was stirred at −78° C. for 30 minutes. At this time, 2-(phenylsulfonyl)benzaldehyde (0.876 g, 3.56 mmol) was added portion-wise as a solution in 2.0 mL DCM. The reaction was monitored by LC/MS. Following addition of the aldehyde, the cold bath was removed and the mixture was stirred overnight (gradually warming to room temp). The reaction was quenched with sodium bircarbonate and moved to a separatory funnel. Layers were separated and the aqueous portion was extracted two additional times with DCM. The organics were combined, dried, filtered, and concentrated. The resulting crude oil was purified via column chromatography (SiO2) using a 0-40% EtOAc/hexane gradient to give ethyl 2-(3-(4-fluorophenyl)-5-methyl-2-phenyl-4-(2-(phenylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (1.0 g, 1.762 mmol, 74.3% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 8.31-8.29 (m, 1H), 7.80-7.78 (m, 2H), 7.53-7.49 (m, 2H), 7.43-7.36 (m, 3H), 7.25-7.21 (m, 4H), 7.10-7.07 (m, 2H), 6.60-6.56 (m, 2H), 6.52-6.48 (m, 2H), 4.49 (s, 2H), 4.21 (q, 2H), 3.97 (s, 2H), 1.86 (s, 3H), 1.26 (t, 3H).

Provenance & Evidence