Diethyl Carbonate → HCID 12971970, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-[2-fluoro-5-(4-morpholinylmethyl)phenyl]-1-ethanone (19.6 g) of Preparation No. 54 in diethyl carbonate (150 mL) is cooled to 0° C., and sodium hydride (60% dispersion, 6.6 g) is added slowly to the reaction mixture. The reaction is stirred at 0° C. for 3 hours, and then is allowed to warm to room temperature overnight. The reaction mixture is quenched with acetic acid (10 mL), diluted with water (200 mL) and then basified with sat. sodium carbonate. The solution is then extracted with ether (3×200 mL). The combined organic layers are washed with sat. sodium bicarbonate (100 mL) and brine (50 mL). The combined aqueous layers are back-extracted with ether (50 mL). The combined organic layers are then dried (Na2SO4) and concentrated in vacuo to an orange oil. The crude product is purified in 2 batches by column chromatography (heptane/IPA, 8/1; 4/1) to afford 20.2 g (79%) of the title compound as a yellow oil.

Provenance & Evidence