Sodium Hydroxide → HCID 22335598, compound

Participants

Reaction Steps

The solution of 2,2,2-trifluoro-1-(3-methyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-2-yl)-ethan-1-one (1.8 g, 6 mmol) in THF (70 ml) is treated successively with trifluoromethyltrimethylsilane (7.5 ml, 2 M in THF, 15 mmol) and tetrabutylammonium fluoride (bound to silica gel, 1.1 mmol/g of SiO2; 0.5 g, 0.55 mmol) and stirred at 40° C. for 2 h (TLC: SiO2/hexane-diethyl ether 1:1; starting material Rf 0.4; product Rf 8.5). The mixture is cooled in an ice bath and treated with NaOH (70 ml, 10% strength solution; 7 g, 175 mmol) and stirred at room temperature for 1 h. The THF phase is treated with diethyl ether (50 ml) and separated in a separating funnel and the aqueous phase is again extracted with diethyl ether (50 ml). The combined organic phases are washed with water (50 ml), dried over Na2SO4 sicc. and concentrated in vacuo.

Provenance & Evidence