Tetrahydrofuran → ethyl N-(diphenylmethylidene)-3-methoxyphenylalaninate

Participants

Reaction Steps

To a 100-mL round-bottomed flask was added 3-methoxybenzyl bromide (0.73 mL, 5.22 mmol, Sigma-Aldrich, St. Louis, Mo.), ethyl N-(diphenylmethylene)glycinate (1.40 g, 5.22 mmol, Acros, Pittsburgh, Pa.), 5 M sodium hydroxide (5.22 mL, 26.1 mmol) and THF (20 mL). The reaction mixture was stirred at room temperature for 2 d. After that time, the mixture was diluted with water (30 mL) and extracted with EtOAc (2×60 mL). The organic extracts were washed with saturated NaCl (30 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as light-yellow oil. Purification by silica gel chromatography, eluting with 20% EtOAc in hexanes gave ethyl N-(diphenylmethylidene)-3-methoxyphenylalaninate (1.56 g).

Provenance & Evidence