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

HRID 1972652Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1972652
Br[CH2:2][C:3]1[C:4]([O:9][CH3:10])=[N:5][CH:6]=[CH:7][CH:8]=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+]>O1CCCC1.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])[CH2:2][C:3]2[C:4]([O:9][CH3:10])=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 575745123-(Bromomethyl)-2-methoxypyridine

Produkt 1

HCID 86670427ethyl N-(diphenylmethylidene)-3-(2-methoxy-3-pyridinyl)alaninateAusbeute 71,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 100-mL round-bottomed flask were added 3-(bromomethyl)-2-methoxypyridine (1.10 g, 5.44 mmol), ethyl N-(diphenylmethylene)glycinate (1.46 g, 5.44 mmol, Acros, N.J.) and 5N sodium hydroxide (5.44 mL, 27.2 mmol) in tetrahydrofuran (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 (20 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as light-yellow oil. The crude product was purified by silica gel chromatography, eluting with 20% EtOAc/hexanes to give ethyl N-(diphenylmethylidene)-3-(2-methoxy-3-pyridinyl)alaninate (1.52 g) as viscous oil.

Aufarbeitung

  1. extractionextracted with EtOAc (2×50 mL)
  2. extractionThe organic extract
  3. washwas washed with saturated NaCl (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customto give the crude material as light-yellow oil
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with 20% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2b0859d8251b438bb91488379ce4442b
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431563B2

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