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

HRID 1057661노트

반응식

HRID 1057661 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-08bdb103813d484fb8ff4d98f91eb2c4
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514968B1

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