Ethylene Glycol → 2-(3,3-Diphenyl-2-propen-1-yloxy)ethanol

Participants

Reaction Steps

A solution of n-butyllithium in hexanes (7.3 ml, 2.5 M) was added drop-wise under a nitrogen atmosphere to ethylene glycol (20 ml) at 10° C. When addition was complete the mixture was stirred for 0.5 h at room temperature. 3-Bromo-1,1-diphenyl-1-propene (5.0 g, 18.3 mmol) was added and the reaction mixture was stirred at room temperature for 1 h, at 80° C. for 0.5 h and finally at room temperature for 3 h. Water (100 ml) was added and the mixture was extracted with ethyl acetate (100 ml). The phases were separated and the organic phase was washed with water (2×50 ml), dried (Na2SO4) and the solvent was evaporated in vacuo. Flash chromatography of the residue on silica gel (150 g) using n-heptane and THF (4:1) as eluent provided 2.9 g (62%) of 2-(3,3-diphenyl-2-propen-1-yloxy)ethanol.

Provenance & Evidence