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

HRID 1672439

反応式

HRID 1672439 の反応式
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

参加物

7

反応物 3

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

生成物 1

HCID 667246621-Trimethylsilanyloxy-4,5-dimethoxyindane-1-carbonitrile収率 73%

試薬・触媒・溶媒 3

HCID 9883512zinc(II)iodide触媒HCID 1140Toluene溶媒2 回HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
50 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-581e6cc5b894409ba8eb0381f926ec24
出典データセット
uspto-grants-2011_08
特許番号
US07998978B2

関連ノート

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