Borane → Ethyl 5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-(ethoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (2.66 g, 8.89 mmol) in dry tetrahydrofuran (40 mL) at 0° C. under an atmosphere of nitrogen was added 1 M of borane solution in tetrahydrofuran (20 mL, 20 mmol). The reaction was stirred at 0° C. for 30 minutes after the addition was complete, and then the cooling bath was removed. After being stirred for 2 hours at room temperature, the reaction mixture was cooled at 0° C. and quenched by addition of 2 M aq. HCl (30 mL). The mixture was stirred for 1 hour at room temperature, and then extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel column to afford the title compound.

Provenance & Evidence