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

HRID 1013576Notes

Reaction equation

HRID 1013576 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-0d563bd69e9c471e9690fe8adab4601e
Source dataset
uspto-grants-2011_07
Patent number
US07981923B2

Reaction notes

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