Selenium Dioxide → 6-Cyclopentyloxy-7-methoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carbaldehyde

HRID 1833161노트

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HRID 1833161 반응식
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][C:16]=2[O:17][CH3:18])[C:13]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)=[N:12][CH:11]=[C:10]3[CH:28]=[O:29])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Se](=O)=[O:31].C(OCC)(=O)C.CCCCCC>C(O)(=O)C>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][C:16]=2[O:17][CH3:18])[C:13]([C:19](=[O:31])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)=[N:12][CH:11]=[C:10]3[CH:28]=[O:29])[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

5

반응물 3

HCID 24007Selenium DioxideHCID 21226206Ethyl acetate hexaneHCID 220484086-Cyclopentyloxy-7-methoxy-1-(3-methoxy-benzyl)-isoquinoline-4-carbaldehyde

생성물 1

HCID 220483816-Cyclopentyloxy-7-methoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carbaldehyde수율 64.1%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
120 °C

실험 절차

To a stirred solution of 6-cyclopentyloxy-7-methoxy-1-(3-methoxy-benzyl)-isoquinoline-4-carbaldehyde (300 mg, 0.77 mmol) in acetic acid (7 μL) was added selenium dioxide (255 mg, 2.30 mmol). The reaction mixture was heated at 120° C. for 1 h. The solvent was evaporated and the residue was diluted with dichloromethane (30 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (20 mL), saturated aqueous sodium chloride solution (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford a crude oil. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 40% ethyl acetate/hexane) afforded 6-cyclopentyloxy-7-methoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carbaldehyde as a yellow solid (200 mg, 64% yield).

후처리

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with dichloromethane (30 mL)
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (20 mL), saturated aqueous sodium chloride solution (20 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a crude oil

출처 및 근거

ORD 기록
ord-2c3616fb8492406885dfec3dacb34322
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067529B2

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