Triethylamine → 4-(2-oxo-2H-pyridin-1-yl)-benzaldehyde

HRID 1271712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271712
[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[C:8]1[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=1.CCN(CC)CC.ClC(OCC)=O.[BH4-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[C:8]1[CH:16]=[CH:15][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 24436Sodium SulfateHCID 4311764Sodium borohydrideHCID 18453190HCID 18453190, Verbindung

Produkt 1

HCID 107031494-(2-oxo-2H-pyridin-1-yl)-benzaldehydeAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 4-(2-oxo-2H-pyridin-1-yl)-benzoic acid (0.31 g, 1.4 mmol) in THF (12 mL) was added Et3N (0.30 mL, 2.15 mmol, 1.5 eq) followed by dropwise addition of ClCOOEt (0.16 mL, 1.2 eq) at 0° C. under N2. The mixture was stirred for 1 h at 0° C., filtered, and rinsed with THF. The THF solution was stirred at 0° C., MeOH (3 mL) was added followed by portionwise addition of NaBH4 (0.26 g, 6.8 mmol). The mixture was stirred at 0° C. for 20 min, sat'd Na2SO4 added, extracted with CH2Cl2, dried (MgSO4), filtered, and concentrated to dryness to give 4-(2-oxo-2H-pyridin-1-yl)-benzaldehyde (0.17 g) as a tan solid.

Aufarbeitung

  1. filtrationfiltered
  2. washrinsed with THF
  3. stirringThe THF solution was stirred at 0° C.
  4. additionMeOH (3 mL) was added
  5. stirringThe mixture was stirred at 0° C. for 20 min
  6. additionadded
  7. extractionextracted with CH2Cl2
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-404e8cac77324a79bf87521223e5956a
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205318B2

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