Ethylene Glycol → HCID 28414031, compound

Participants

Reaction Steps

NaH (2.4 g of a 60% suspension in mineral oil, 60 mmol) was washed twice with heptane (2×20 mL). Dry THF (20 mL) and ethylene glycol (24.8 g, 400 mmol) were added in portions over the course of 15 minutes (which resulted in an exothermic reaction and the evolution of gas). The resulting mixture was stirred for 2 h at RT. The mixture was then warmed to 80° C. and, after 20 minutes, benzyl bromide (7.84 g, 40 mmol) was added in portions over the course of 60 minutes. The reaction mixture was then stirred at 80° C. for 2 h, before being cooled to RT. Saturated NH4Cl solution (150 mL) was added slowly and the resulting mixture was extracted with diethyl ether (3×100 mL), washed with aqueous NH4Cl solution and brine, dried over Na2SO4 and then evaporated and purified by chromatography on silica (heptane: ethyl acetate (60:40) eluent). This gave 5.5 g (76.5%) of the sub-title compound.

Provenance & Evidence