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

HRID 252280Notes

Reaction equation

HRID 252280 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-9470ec3de1874f9d8332871b4f4afd92
Source dataset
uspto-grants-2011_01
Patent number
US07868031B2

Reaction notes

Loading…