Carbonyl bromide → 2-(4-Methylsulphinylphenyl)-1-phenyl-6,7-dihydro-5H-pyrrolizine

Participants

Reaction Steps

2-Benzyl-1-pyrroline (2.0 g, 80% strength, 10 mmol), dissolved in MeOH (30 ml), is treated with a solution of 4-methylsulphinylphenacyl bromide (2.1 g, 8 mmol) in CH2Cl2 (10 ml) and then with NaHCO3 (1.5 g, 18 mmol) and the mixture is stirred at RT until a TLC sample (Al2O3, hexane/ether 9:1) indicates the complete reaction of the bromoketone (Rf 0.75) and an adequate formation of product (Rf=0.2) (48 h). After addition of water (50 ml), the mixture is extracted with diethyl ether (3×30 ml), and the combined extracts are dried over Na2SO4 sicc. and concentrated. The residue is purified by CC (Al2O3, hexane/ether 1:1). 0.3 g (12%) of the compound sought is isolated.

Provenance & Evidence