Diisobutylaluminum hydride → [1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-methanol

HRID 1698229

Reaktionsgleichung

Reaktionsgleichung von HRID 1698229
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:10]=1)=O)C.CC(C[AlH]CC(C)C)C>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:17]1([CH3:20])[CH:16]=[CH:15][C:14]([S:11]([N:9]2[CH:10]=[C:6]([CH2:4][OH:3])[CH:7]=[N:8]2)(=[O:13])=[O:12])=[CH:19][CH:18]=1

Komponenten

5

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 216282771-(toluene-4-sulfonyl)-1H-pyrazole-4-carboxylic acid ethyl ester

Produkt 1

HCID 59278506[1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a chilled (−78° C.) solution of 1-(toluene-4-sulfonyl)-1H-pyrazole-4-carboxylic acid ethyl ester (0.90 g, 3.06 mmol) in CH2Cl2 was added a 1 M solution of DIBAH (11.00 mL, 11.00 mmol) in CH2Cl2 dropwise. After 4 hours, the reaction was warmed to room temperature. After 8 hours, the mixture was diluted with saturated aqueous NaHCO3. After 2 hours, the solution was passed through the diatomaceous earth. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the [1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-methanol.

Aufarbeitung

  1. waitAfter 8 hours
  2. waitAfter 2 hours
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4c8523e2493d462896739494dbc60d82
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163918B2

Verknüpfte Notizen

Wird geladen…