Sulfuric Acid → Cyclobutanecarboxaldehyde, 1-[2-(trifluoromethyl)phenyl]-

HRID 1393910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1393910
[H-].C([Al+]CC(C)C)C(C)C.[F:11][C:12]([F:26])([F:25])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1([C:23]#N)[CH2:22][CH2:21][CH2:20]1.S(=O)(=O)(O)[OH:28]>C1(C)C=CC=CC=1>[F:11][C:12]([F:26])([F:25])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1([CH:23]=[O:28])[CH2:22][CH2:21][CH2:20]1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 21225700DiisobutylaluminumhydrideHCID 596809531-[2-(Trifluoromethyl)phenyl]cyclobutanecarbonitrile

Produkt 1

HCID 59680954Cyclobutanecarboxaldehyde, 1-[2-(trifluoromethyl)phenyl]-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

50.7 ml of diisobutylaluminum hydride was added dropwise over 2 hours to a solution of 8.5 g of 1-(2-trifluoromethyl-phenyl)-cyclobutanecarbonitrile in 85 ml toluene at 0° C. After addition, the ice-water bath was allowed to warm up to room temperature slowly and the reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into 200 ml of 5% sulfuric acid in ice-water, and stirred for 10 minutes. The mixture was extracted four times with ether. The combined ether extracts were dried and concentrated by evaporation in a vacuum. The residue was purified by column chromatography on silica-gel (EtOAc-hexane 5%) to yield 6.2 g of product.

Aufarbeitung

  1. additionAfter addition
  2. stirringstirred for 10 minutes
  3. extractionThe mixture was extracted four times with ether
  4. dry with materialThe combined ether extracts were dried
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe residue was purified by column chromatography on silica-gel (EtOAc-hexane 5%)

Quellen und Nachweise

ORD-Eintrag
ord-3b826ba60d8544cfafd1a5cf78fd8b9b
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348322B2

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