Acetonitrile → 1-Trimethylsilanyloxy-4,5-dimethoxyindane-1-carbonitrile

HRID 1672439

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HRID 1672439 반응식
C[Si:2]([C:5]#N)([CH3:4])[CH3:3].[CH3:7][O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][C:13]2=[O:20].[C:21](#[N:23])C>C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+].[I-].[Zn+2].[I-]>[CH3:5][Si:2]([CH3:3])([CH3:4])[O:20][C:13]1([C:21]#[N:23])[C:14]2[C:10](=[C:9]([O:8][CH3:7])[C:17]([O:18][CH3:19])=[CH:16][CH:15]=2)[CH2:11][CH2:12]1

참가 물질

7

반응물 3

HCID 6342AcetonitrileHCID 82115Trimethylsilyl cyanideHCID 2404464,5-Dimethoxy-1-indanone

생성물 1

HCID 667246621-Trimethylsilanyloxy-4,5-dimethoxyindane-1-carbonitrile수율 73%

시약·촉매·용매 3

HCID 9883512zinc(II)iodide촉매HCID 1140Toluene용매2회HCID 516892Sodium Bicarbonate용매

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온도
50 °C

실험 절차

Under nitrogen, zinc iodide (1.5 g, 4.68 mmol), trimethylsilyl cyanide (27.1 mL, 203.0 mmol) were added sequentially to the solution of 4,5-dimethoxy-1-indanone (30.0 g, 156.1 mmol) in toluene (100 mL) and acetonitrile (24 mL). The reaction mixture was heated to 50° C. for 16 h. The reaction mixture was cooled to room temperature and diluted with 100 mL of toluene and 60 mL of a saturated aqueous sodium bicarbonate solution. After the mixture was stirred for 1 h, the layers were separated. The organic layer was washed by brine (60 mL) and dried (Na2SO4). The organic layer was concentrated in vacuo and the residue was purified by chromatography (EtOAc/Hexanes: 5/95) to afford 1-trimethylsilanyloxy-4,5-dimethoxyindane-1-carbonitrile (33.1 g, 73%).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe layers were separated
  3. washThe organic layer was washed by brine (60 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe residue was purified by chromatography (EtOAc/Hexanes: 5/95)

출처 및 근거

ORD 기록
ord-581e6cc5b894409ba8eb0381f926ec24
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998978B2

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