Ethylene Glycol → 2-(3-(2-Methylphenyl)-3-phenyl-2-propen-1-yloxy)ethanol

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Reaction Steps

A solution of n-butyllithium in hexanes (13.0 ml, 2.5 M) was added dropwise under a nitrogen atmosphere to ethylene glycol (30 ml) at 10° C. When addition was complete the mixture was stirred 0.5 h at room temperature. 3-Bromo-1-(2-methylphenyl)-1-phenyl-1-propene (9.3 g, 32 mmol) was added and the reaction mixture was stirred at room temperature for 100 h. The mixture was poured into water (200 ml) and extracted with ethyl acetate (3×75 ml). The combined organic extracts was dried over sodium sulphate and the solvent evaporated in vacuo. Flash chromatography of the residue on silica gel (200 g) using a mixture of n- heptane and THF (4:1) as eluent provided 3.9 g (45%) of 2-(3-(2-methylphenyl)-3-phenyl-2-propen-1-yloxy)ethanol. TLC: rf=0.20 (SiO2 ; n-heptane/THF=7:3).

Provenance & Evidence