Potassium Carbonate → [(9-Benzyl-7-methoxy-9H-carbazol-4-yl)oxy]acetonitrile

HRID 1057661ノート

反応式

HRID 1057661 の反応式
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:21])[C:15]=2[C:14]2[C:9]1=[CH:10][C:11]([O:22][CH3:23])=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][C:32]#[N:33]>CN(C=O)C>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:31][C:32]#[N:33])[C:15]=2[C:14]2[C:9]1=[CH:10][C:11]([O:22][CH3:23])=[CH:12][CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 186716949-Benzyl-7-methoxy-9H-carbazol-4-ol

生成物 1

HCID 18671671[(9-Benzyl-7-methoxy-9H-carbazol-4-yl)oxy]acetonitrile収率 94%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 9-benzyl-7-methoxy-9H-carbazol-4-ol (0.86 g, 2.8 mmol) in DMF (30 mL) is added potassium carbonate (1.17 g, 8.5 mmol) and bromoacetonitrile (0.56 mL, 8.0 mmol). The mixture is stirred at room temperature for 18 h. The mixture is partitioned between water and CH2Cl2. The layers are separated and the organic layer washed twice with water (100 mL). The organic layer is dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography (100 mL) silica gel using CH2Cl2 as eluent gave 0.9 g (94%) of the title compound; 1H NMR (CDCl3) δ3.86, 5.04, 5.46, 6.73, 6.82, 6.87, 7.05, 7.14, 7.28, 8.15; Anal. Calcd for C22H18N2O2: C, 77.17; H, 5.30; N, 8.18. Found: C, 76.00; H, 5.32; N, 8.43.

後処理

  1. customThe mixture is partitioned between water and CH2Cl2
  2. customThe layers are separated
  3. washthe organic layer washed twice with water (100 mL)
  4. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-08bdb103813d484fb8ff4d98f91eb2c4
出典データセット
uspto-grants-2003_02
特許番号
US06514968B1

反応ノート

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