2-[(4-methoxyphenyl)methoxymethyl]oxirane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Thiourea (0.935 g, 12.28 mmol) was added to a solution of 2-(((4-methoxybenzyl)oxy)methyl) oxirane (1.084 g, 5.58 mmol) in methanol (30 mL) and the mixture stirred at room temperature for 16 hours, then evaporated under vacuum. Purification by chromatography on silica, eluting with 0-10% EtOAc/hexane, afforded the title compound. evaporated under vacuum Purification by chromatography on silica eluting with 0-10% EtOAc/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: p-Methoxybenzyl chloride (2.326 g, 14.85 mmol) was added slowly to a suspension of sodium hydride (60% dispersion in mineral oil, 0.594 g, 14.85 mmol) in DMF (25 mL) at 0° C. and the mixture stirred for 25 mins. Glycidol (1 g, 13.50 mmol) was then added dropwise over 25 mins, the mixture was allowed to warm to room temperature and stirred for 3 days. The mixture was diluted with EtOAc (50 ml) and washed with saturated NH4Cl (aq) (30 ml), saturated NaHCO3 (aq) (50 ml) and brine (100 ml). The organic phase was dried over magnesium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-10% EtOAc/hexane, afforded the title compound. stirred for 3 days washed with saturated NH4Cl (aq) (30 ml), saturated NaHCO3 (aq) (50 ml) and brine (100 ml) The organic phase was dried over magnesium sulfate evaporated under vacuum Purification by chromatography on silica eluting with 0-10% EtOAc/hexane