Triethylsilane → HCID 53246024, compound

Participants

Reaction Conditions

Reaction Steps

In a scintillation vial, ethyl 2-(5-methyl-2,3-diphenyl-1H-pyrrol-1-yl)acetate (0.3 g, 0.939 mmol) was dissolved in 10 mL of DCM and the mixture cooled to −78° C. Trimethylsilyl trifluoromethanesulfonate (0.382 ml, 2.113 mmol) was then added followed by triethylsilane (0.450 ml, 2.82 mmol). The resulting mixture was stirred at −78° C. for 30 minutes. At this time, 2-(phenylsulfonyl)benzaldehyde (0.231 g, 0.939 mmol) was added portionwise as a solution in 2.0 mL of DCM and the reaction evolution was monitored by LC/MS. Following addition of the aldehyde, the cold bath was removed and the reaction was stirred overnight (gradually warming to room temp). The reaction was quenched with a sodium bircarbonate solution and moved to a separatory funnel. Layers were separated and the aqueous portion was extracted 2 additional times with DCM. The organics were combined, dried, filtered, and concentrated. The crude oil was purified by column chromatography (SiO2) using a 0-40% EtOAc/hexane gradient to give ethyl 2-(2-methyl-4,5-diphenyl-3-(2-(phenylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (294 mg, 0.535 mmol, 56.9% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 8.31-8.29 (m, 1H), 7.84-7.82 (m, 2H), 7.52-7.48 (m, 2H), 7.42-7.38 (m, 3H), 7.28-7.21 (m, 4H), 7.15-7.13 (m, 2H), 6.93-6.86 (m, 3H), 6.75-6.73 (m, 2H), 4.51 (s, 2H), 4.21 (q, 2H), 4.04 (s, 2H), 1.79 (s, 3H), 1.25 (t, 3H).

Provenance & Evidence