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

HRID 1972669Notes

Reaction equation

HRID 1972669 reaction equation
BrC[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([O:9][CH3:10])[CH:4]=1.[C:11]1([C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+].[CH2:33]1COCC1>O>[C:11]1([C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:18][C@H:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:33][C:7]2[CH:8]=[CH:3][CH:4]=[C:5]([O:9][CH3:10])[N:6]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 198054314-(Bromomethyl)-2-methoxypyridine

Product 1

HCID 86670428ethyl N-(diphenylmethylidene)-3-(6-methoxy-2-pyridinyl)alaninate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100-mL round-bottomed flask were added 4-(bromomethyl)-2-methoxypyridine (1.98 g, 9.80 mmol), ethyl N-(diphenylmethylene)glycinate (2.62 g, 9.80 mmol, Acros, N.J.) and 5N sodium hydroxide (9.80 mL, 49.0 mmol) in THF (20 mL). The reaction mixture was stirred at room temperature for 24 h, 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 20% EtOAc/hexanes to give ethyl N-(diphenylmethylidene)-3-(6-methoxy-2-pyridinyl)alaninate (2.58 g) as a light-yellow oil.

Workup

  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 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-cf2fd42676234d5fa48fc0dce92b5630
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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