Dimethylformamide → (RS)-2-biphenyl-4-yl-2-ethoxy-propionic acid ethyl ester

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Reaction Steps

To a solution of 2-biphenyl-4-yl-2-hydroxy-propionic acid (CAS-6244-54-8, 943 mg) in THF (10 ml), stirred at 0° C. was added NaH (60% in mineral oil, 342 mg). After 50 min, ethyl iodide (0.69 ml) was added and the mixture was stirred at rt for 14 h. DMF (10 ml) was added. After 2 days, 47 mg NaH and 0.16 ml ethyl iodide were added subsequently. In the course of three weeks, a total of 653 mg NaH and 1.32 ml ethyl iodide were added. Water was added and the mixture was extracted with EtOAc (2×). The organic phase was washed with water, dried, filtered and evaporated. The crude product was purified by flash chromatography (EtOAc/cyclohexane 5:95=>1:4) to give (RS)-2-biphenyl-4-yl-2-ethoxy-propionic acid ethyl ester (276 mg) as a light yellow oil. MS 298.1 ([M]+)

Provenance & Evidence