Diisobutylaluminum hydride → 5-(4-Chlorophenyl)oxazole-4-carbaldehyde

HRID 1506661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1506661
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][CH:11]=[N:10][C:9]=2[C:13](OCC)=[O:14])=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][CH:11]=[N:10][C:9]=2[CH:13]=[O:14])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 2739479Ethyl 5-(4-chlorophenyl)oxazole-4-carboxylate

Produkt 1

HCID 153155355-(4-Chlorophenyl)oxazole-4-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

To a solution of 33C (1.25 g, 5 mmol) in THF was added DIBAL-H (1.0 M in toluene, 10 mmol) dropwise at −70° C. The resulting solution was allowed to warm to −20° C. over 3 h. Upon completion of the reaction, saturated aqueous NH4Cl was added to the flask and the mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was used in the next step without further purification. MS (m/z) 208.1 [M+H]+.

Aufarbeitung

  1. additionwas added to the flask
  2. customthe mixture was partitioned between EtOAc and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-87a12a81f3ff4951aaca26b829b1799c
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09220710B2

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