Sodium Carbonate → 2,5-Dimethyl-1-phenyl-3-vinyl-1H-pyrrole

Participants

Reaction Steps

To a solution of bromomethyl(triphenyl)phosphonium bromide (2.2 g, 5 mmol) in dry THF (50 mL), n-Bu.Li (2.5 M, 2 mL, 5 mmol) was added dropwise at −78° C. under nitrogen. The reaction mixture was stirred 30 min at this temperature and compound 5 (1.0 g, 5 mmol) was added, then the cooling bath was removed. Stirring was continued for another hour. The solvent was completely removed under reduced pressure. The residue and Pd(OAc)2 (56 mg, 0.25 mmol), Na2CO3 (1.86 g, 17.5 mmol), n-Bu4NCl (8.34 g, 30 mmol) were dissolved in dried DMF (20 mL). The reaction mixture was stirred at 100° C. for 3 hrs. The reaction was quenched by adding 20 mL of water, and the aqueous phase was extracted with EtOAc (30 mL×3). The combined extracts were dried over Na2SO4, the mixture was filtered and the filtrate was concentrated in vacuo to give the desired product as a colorless oil (Purity: 90%, yield: 80%). MS [M++1]=198, LC-MS: tR=2.76 min.

Provenance & Evidence