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

HRID 339177노트

반응식

HRID 339177 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 9883512zinc(II)iodide촉매HCID 3283Diethyl Ether용매

실험 절차

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 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)+.

후처리

  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 the solvent was removed under reduced pressure
  9. washThe crude product was eluted through silica under medium pressure with 5% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-1d2cf67b3f3a4bf48c1c698ce3d63b63
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889906B2

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