Hydrochloric Acid → 4-(5-Fluoro-2-methoxyphenyl)butanal

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl-4-(5′-fluoro-2′-methoxyphenyl)butyrate (2.25 g, 9.4 mmol) in dry toluene (30 mL) under Ar(g) was added DIBAL solution (1 M in toluene, 11 mL, 11 mmol) at −78° C. Then the reaction was stirred at this temperature for 2 h. Methanol (2 mL) was then added to the reaction mixture and the reaction was allowed to warm to 0° C. The reaction mixture was poured into a separatory funnel containing HCl solution (1 N, 100 mL). The organic function was extracted with ethyl acetate (3×60 mL) and the combined organic layers were washed with brine (80 mL) and dried over sodium sulfate. The crude product that obtained by removal of the solvent in vacuo was purified by flash column chromatography (10% EtOAc in hexane, Rf=0.10) to give the product (1.30 g, 70%).

Provenance & Evidence