Methanol → HCID 21470369, compound

Participants

Reaction Conditions

Reaction Steps

In a stream of argon gas, 1-bromo-2-(biphenyl-4-yloxymethyl)benzene (16.96 g, 0.05 mol) in dry THF (70 ml) was dropwise added to a mixture of magnesium (2.43 g, 0.1 mol) and dibromoethane (0.1 ml) in dry THF (10 ml) at 50° to 60° C. over 20 minutes. The reaction mixture was stirred at 65° C. for 1 hour, diluted with dry THF (20 ml) and cooled below 20° C. The mixture was dropwise added to oxalyl chloride (7.61 g, 0.06 mol) in dry THF (150 ml) below -15° C. over 15 minutes, followed by stirring at -75° C. for 1 hour, and anhydrous methanol (12.82 g, 0.4 mol) was added thereto below -50° C., followed by stirring at room temperature for 1 hour. After completion of the reaction, aqueous ammonium chloride (500 ml) was added to the reaction mixture which was then extracted with ether (400 ml). The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/toluene) to give methyl 2-[2-(biphenyl-4-yloxymethyl)phenyl]-2-oxoacetate (11.79 g; yield, 68.1%) as pale yellow crystals.

Provenance & Evidence