反应详情

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).

1. extractionextracted with EtOAc (2×60 mL)
2. washThe organic extracts were washed with saturated NaCl (30 mL)
3. dry with materialdried over Na2SO4
4. filtrationThe solution was filtered
5. concentrationconcentrated in vacuo
6. customto give the crude material as light-yellow oil
7. customPurification by silica gel chromatography
8. washeluting with 20% EtOAc in hexanes