Trimethylsilyl cyanide → 6-Benzenesulfonyl-3,4-dihydro-naphthalene-1-carbonitrile

HRID 420186Notes

Reaction equation

HRID 420186 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16](=O)[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([C:25]#[N:26])(C)C>[I-].[Zn+2].[I-].CCOCC>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([C:25]#[N:26])=[CH:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 590217396-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 590217566-Benzenesulfonyl-3,4-dihydro-naphthalene-1-carbonitrileYield 44%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 3283Diethyl EtherSolvent

Procedure

6-Benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-one from Preparation 1 above (4.0 g, 14 mmol), trimethylsilyl cyanide (10.0 g, 100 mmol) and Zinc Iodide (0.25 g) were combined and stirred under nitrogen for 15 hours. The reaction mixture was then diluted by addition of 200 mL of Et2O, washed with cold water, and the organic layer was dried (MgSO4) and evaporated under reduced pressure to an oil. The oil was dissolved in 250 mL of toluene, and 0.5 g of paratoluene sulfonic acid was added. The reaction mixture was refluxed for three hours, cooled, and the solvent was removed under reduced pressure. The crude product was eluted through silica under medium pressure with 5% EtOAc in hexanes to yield 1.8 g (6.1 mmol, 44%) of (racemic) 6-benzenesulfonyl-3,4-dihydro-naphthalene-1-carbonitrile as an oil. MS: 296 (M+H)+.

Workup

  1. washwashed with cold water
  2. dry with materialthe organic layer was dried (MgSO4)
  3. customevaporated under reduced pressure to an oil
  4. dissolutionThe oil was dissolved in 250 mL of toluene
  5. addition0.5 g of paratoluene sulfonic acid was added
  6. temperatureThe reaction mixture was refluxed for three hours
  7. temperaturecooled
  8. customthe solvent was removed under reduced pressure
  9. washThe crude product was eluted through silica under medium pressure with 5% EtOAc in hexanes

Sources & evidence

ORD record
ord-02ec084aaf22484e851d5b69bf3177a9
Source dataset
uspto-grants-2012_01
Patent number
US08093424B2

Reaction notes

Loading…