Water → 3-Methoxy-4-pyridin-2-ylbenzaldehyde

HRID 2213099Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2213099
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[C:6]#N.[H-].[OH2:18]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[CH:6]=[O:18]

Komponenten

5

Edukt 3

HCID 962WaterHCID 166653HydrideHCID 21956523HCID 21956523, Verbindung

Produkt 1

HCID 219565123-Methoxy-4-pyridin-2-ylbenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of 3-methyoxy-4-pyridin-2-ylbenzonitrile (600 mg, 2.64 mmol) in CH2Cl2 (10 mL) was cooled to −78° C. and was treated with diisobutylalumnium hydride (3.2 mL of 1M in CH2Cl2, 3.2 mmol). After stirring the reaction mixture at −78° C. for 2 h, the temperature was raised to −40° C. before quenching the reaction with a mixture of silica gel (6 g) and water (2 mL) and then warmed to rt. The reaction mixture was dried (K2CO3 and MgSO4), and concentrated. The residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:4 to 1:1) to afford 3-methoxy-4-pyridin-2-ylbenzaldehyde.

Aufarbeitung

  1. temperaturethe temperature was raised to −40° C.
  2. custombefore quenching
  3. customthe reaction
  4. temperaturewarmed to rt
  5. dry with materialThe reaction mixture was dried (K2CO3 and MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:4 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-9774da904bc6423caac1cb8d54730f50
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105533B2

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