StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

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

HRID 1972669
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1972669
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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cf2fd42676234d5fa48fc0dce92b5630
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08431563B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion