HCID 10832317, compound → HCID 10546597, compound

HRID 1780846Notes

Reaction equation

HRID 1780846 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][CH3:16])=[C:11]([O:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[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][CH3:16])=[C:11]([O:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:10]=2)([CH:23]=[O:38])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 10832317HCID 10832317, compoundHCID 21225700DiisobutylaluminumhydrideHCID 23665763Sodium Bisulfite

Product 1

HCID 10546597HCID 10546597, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one dimethyl ketal (0.57 g, 1.6 mmol) in toluene (20 mL) at room temperature under an argon atmosphere was treated with a solution of diisobutylaluminum hydride (1.5M in toluene, 2.7 mL, 4 mmol). After 2 h, a solution of saturated aqueous sodium bisulfite was added and the mixture was extracted twice with ethyl acetate. The organic extract was washed with 5% aqueous sodium carbonate, was dried (potassium carbonate) and the solvent was removed in vacuo to provide an oil (0.55 g, 96%).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with 5% aqueous sodium carbonate
  4. dry with materialwas dried (potassium carbonate)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e4d05faeef914b90bf8bc2d08ec81875
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

Loading…