Reaction #1797

Reaction equation

H2O CH3CN

HCl

methyl 5-fluoro-2-methoxy-4-[1-(S)-(4-pyridyl)ethoxy]benzoate

NaOH

→

5-fluoro-2-methoxy-4-[1-(S)-(4-pyridyl)ethoxy]benzoic acid

Solvents

methanol

Conditions

Workup

1. 1
   Temperatureheated to 45° C. in an oil bath for another 24 h

Procedure

To a stirred solution of methyl 5-fluoro-2-methoxy-4-[1-(S)-(4-pyridyl)ethoxy]benzoate (290 mg, 0.95 mmol) in methanol (5 mL) was added aqueous NaOH (396 μL, 3.6M). The reaction was stirred at ambient temperature overnight and then heated to 45° C. in an oil bath for another 24 h. The reaction pH was lowered to pH 3 using 1N HCl and the reaction mixture stripped down under reduced pressure. The white foam was lyophilized from H2O/CH3CN to afford the 5-fluoro-2-methoxy-4-[1-(S)-(4-pyridyl)ethoxy]benzoic acid as a white powder.

Source