p-Toluenesulfonic acid → 1-Cyano-5-methoxy-3-phenyl-3,4-dihydronaphthalene

HRID 982122Notes

Reaction equation

HRID 982122 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:7][C:8]2=O.C[Si]([C:24]#[N:25])(C)C.[Cl-].[Al+3].[Cl-].[Cl-].FC(F)(F)C(O)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:24]([C:8]1[C:9]2[C:4](=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][CH:10]=2)[CH2:5][CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=1)#[N:25]

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 6422Trifluoroacetic acidHCID 82115Trimethylsilyl cyanideHCID 6451240Aluminum(III) ChlorideHCID 122124065-Methoxy-3-phenyl-1-tetralone

Product 1

HCID 200690311-Cyano-5-methoxy-3-phenyl-3,4-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of 8.8 g (35 mmol) of 5-methoxy-3-phenyl-1,2,3,4-tetrahydro-1-naphthalenone, the product of Example 1, is added 7.5 g (75.6 mmol) of trimethylsilyl cyanide (commercially available from Aldrich Chemical Company) and approximately 50 mg of anhydrous aluminum chloride (AlCl3). The reaction mixture is heated at 60° C. for 3 h then cooled to ambient temperature and diluted with 150 mL of toluene. The volume of the reaction mixture is reduced in vacuo to approximately 50 mL. The resultant trimethylsilyl adduct is dehydrated by treatment with 15 mL of trifluroacetic acid and 100 mg of p-toluenesulfonic acid in 200 mL of toluene at reflux temperature for 1 h. The reaction mixture is cooled to ambient temperature, the layers separated and the organic layer washed with water, aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound.

Workup

  1. temperaturethen cooled to ambient temperature
  2. temperatureat reflux temperature for 1 h
  3. temperatureThe reaction mixture is cooled to ambient temperature
  4. customthe layers separated
  5. washthe organic layer washed with water, aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3bd7097a258540228997ed72f547d093
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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