Sodium → HCID 20156956, compound

Participants

Reaction Steps

Sodium (2.18 g, 35 mmol) was added to diethyl 4-ethoxyphenylmalonate (26.6 g, 95 mmol) dissolved in dioxane (100 ml) and refluxed until the sodium had dissolved. Chloromethyl(4-fluoro-3-phenoxybenzyl)ether (25.4 g, 95 mmol) was added, dropwise, at 40°-50° C. and then heated under reflux for 3 hours. The mixture was added to ice-water, extracted three times with ether, the extracts washed with water, dried over magnesium sulphate and evaporated. After chromatography on silica-gel, using toluene as the eluent, there was obtained 25.3 g of diethyl 2-(4-ethoxyphenyl)-2-(4-fluoro-3-phenoxybenzyloxymethyl)malonate (52% of theory). This was then reduced in a similar manner to Example 1 using lithium aluminium hydride to give crude 2-(4-ethoxyphenyl)-2-(4-fluoro-3-phenoxybenzyloxymethyl)propane-1,3-diol.

Provenance & Evidence