2-Phenylpropionic acid → HCID 68871308, compound

Participants

Reaction Steps

Lithium bis(trimethylsilyl)amide (3.23 g, 19.3 mmol) was added to 8 mL of tetrahydrofuran and the resulting solution was cooled in an ice bath. Addition of a solution of 2-phenyl-propionic acid (1.16 g, 7.73 mmol) in 1 mL of tetrahydrofuran to the reaction solution was followed by addition of (S)-1-bromo-3-methyl-pentane (2.05 g, 12.4 mmol). The reaction vessel was removed from the cooling bath, placed in a 50° C. oil bath, and the reaction solution was stirred for 17 hours. After concentration, the resulting residue was dissolved in 25 mL of 1 N NaOH, washed with 25 mL of 2:1 hexane/iso-propyl acetate, acidified to pH 1 with 6 N HCl, and extracted with ethyl acetate (3×30 mL). The combined organic layers were dried over Na2SO4 and concentrated to give 1.63 g (90%) of a clear oil. 1H NMR (300 MHz, CDCl3): δ ppm 0.83 m, 6 H) 1.20 m, 5 H) 1.57 (s, 3 H) 1.98 m, 2 H) 7.35 m, 5 H).

Provenance & Evidence