Sodium Hydroxide → ethyl N-(diphenylmethylidene)-3-(6-methoxy-2-pyridinyl)alaninate

To a 100-mL round-bottomed flask was added 2-(bromomethyl)-6-methoxypyridine (1.33 g, 6.58 mmol), 2-(bromomethyl)-6-methoxypyridine (1.33 g, 6.58 mmol), ethyl N-(diphenylmethylene)glycinate (1.76 g, 6.58 mmol, Acros, N.J.) and 5N sodium hydroxide (6.58 mL, 32.9 mmol) in THF (30 mL). The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (2×50 mL). The organic extract was washed with saturated NaCl (30 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow oil. The crude product was purified by silica gel chromatography, eluting with 10% EtOAc/hexanes to give ethyl N-(diphenylmethylidene)-3-(6-methoxy-2-pyridinyl)alaninate (1.86 g) as a colorless oil.

1. extractionextracted with EtOAc (2×50 mL)
2. extractionThe organic extract
3. washwas washed with saturated NaCl (30 mL)
4. dry with materialdried over Na2SO4
5. filtrationThe solution was filtered
6. concentrationconcentrated in vacuo
7. customto give the crude material as a light-yellow oil
8. customThe crude product was purified by silica gel chromatography
9. washeluting with 10% EtOAc/hexanes

ORD record

ord-86771e13fcea4afb86997fc313ef4865

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08431563B2