Diisobutylaluminumhydride → HCID 23222723, compound

HRID 1780854Notes

Reaction equation

HRID 1780854 reaction equation
[CH3:1][O:2][C:3]1([O:25][CH3:26])[CH2:8][CH2:7][C:6]([C:23]#N)([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:18])[F:17])=[C:11]([O:19][CH:20]([F:22])[F:21])[CH:10]=2)[CH2:5][CH2:4]1.[H-].C([Al+]CC(C)C)C(C)C.S(=O)(O)[O-:38].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1([O:25][CH3:26])[CH2:8][CH2:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:18])[F:17])=[C:11]([O:19][CH:20]([F:22])[F:21])[CH:10]=2)([CH:23]=[O:38])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 21225700DiisobutylaluminumhydrideHCID 23222722HCID 23222722, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 23222723HCID 23222723, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-cyano-4-(3,4-bisdifluoromethoxyphenyl)cyclohexan-1-one dimethyl ketal (1.5 g, 3.98 mmol) in toluene (50 mL) at room temperature under an argon atmosphere was treated with a solution of diisobutylaluminum hydride (1M in toluene, 10 mL, 10 mmol). After 4 h, a solution of saturated aqueous sodium bisulfite was added and the mixture was extracted twice with ethyl acetate. The combined organic extract was dried (potassium carbonate) and the solvent was removed in vacuo to provide an oil (1.5 g, 99%).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. extractionThe combined organic extract
  3. dry with materialwas dried (potassium carbonate)
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7cd4f63036e44a77b99c036372397520
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

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