Potassium Fluoride → Methyl 4-cyclopropyl-3-(2-fluoro-3-hydroxyphenyl)butanoate

Participants

Reaction Steps

A 250 mL round bottom flask was charged with 84.D (4.95 g, 13.6 mmol) and MeOH (60 mL) and flushed with N2. To the solution were added magnesium turnings (0.990 g, 40.7 mmol) in one portion (a few turnings were fractured by hammering prior to addition to expose clean metallic edges). The gently bubbling mixture was stirred overnight at room temperature. To the mixture was added potassium fluoride (0.789 g, 13.6 mmol). The resulting mixture was stirred for 1 hour, quenched with 1 N HCl (90 mL), and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water (2×50 mL) and brine (1×50 mL), dried (MgSO4), and concentrated. The residue was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford 84.E (2.70 g, 79% yield) as a yellow oil.

Provenance & Evidence