Diethyl Carbonate → HCID 68597039, compound

Participants

Reaction Conditions

Reaction Steps

To a slurry of sodium hydride (60% oily dispersion; 1.49 g, 37 mmol) and diethylcarbonate (6.0 mL, 49 mmol) in anhydrous THF (70 mL), a solution of 1-(5-bromo-2-(methoxymethoxy)phenyl)ethanone (15, 4.435 g, 17.1 mmol) in anhydrous THF (30 mL) was added in one portion at rt under a nitrogen atmosphere. The mixture was stirred at 80° C. for 5 h. As the reaction was deemed complete by LC-MS, the mixture was cooled to room temperature and quenched by pouring it onto 1:1 ice/1N NaHSO4 (100 mL). Extractions with Et2O (2×150 mL) followed. The combined organic layers were washed with water (80 mL), brine (60 mL), and then dried over MgSO4. After purification by flash chromatography (9:1 to 8:2 hexane/EtOAc), the title compound (16) was obtained as colorless oil (4.403 g, 78% yield).

Provenance & Evidence