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

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.

1. customflushed with N2
2. additionto addition
3. customThe gently bubbling mixture
4. stirringThe resulting mixture was stirred for 1 hour
5. customquenched with 1 N HCl (90 mL)
6. extractionextracted with EtOAc (2×50 mL)
7. washThe combined organic layers were washed with water (2×50 mL) and brine (1×50 mL)
8. dry with materialdried (MgSO4)
9. concentrationconcentrated
10. customThe residue was purified by silica gel flash chromatography (0-20% EtOAc/hexane)

ORD record

ord-52e1b91e38154e8682bf59e785ec876a

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030354B2