Methyl iodide → (R)-4-(4-Fluoro-3-methylphenyl)-4-methoxybutanoic acid

Participants

Reaction Steps

To the suspension of NaH (373 mg of a 60% dispersion in mineral oil, 9.3 mmol) in 20 mL THF was slowly added (R)-4-(4-Fluoro-3-methyl-phenyl)-4-hydroxy-butanoic acid as a solution in 10 mL THF at 25° C. Methyl iodide (974 mg, 6.9 mmol, 427 μL) was then added dropwise to the mixture. The resulting mixture was stirred for 3 h at room temperature and then the reaction was quenched by the addition of 20 mL of 1M HCl. The mixture was and extracted with ethyl acetate (3×30 mL) and the combined organic layers washed with brine (2×20 mL) and dried over sodium sulfate. Evaporation of solvent left the crude product as an oil which was used in the next step without further purification.

Provenance & Evidence