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

HRID 1833151노트

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HRID 1833151 반응식
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[C:12]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)=[N:11][CH:10]=[C:9]2[CH:27]=[O:28])[CH2:2][CH2:3][CH3:4].[Se](=O)=[O:30].C(OCC)(=O)C.CCCCCC>C(O)(=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[C:12]([C:18](=[O:30])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)=[N:11][CH:10]=[C:9]2[CH:27]=[O:28])[CH2:2][CH2:3][CH3:4]

참가 물질

5

반응물 3

HCID 24007Selenium DioxideHCID 21226206Ethyl acetate hexaneHCID 220482946-Butoxy-7-methoxy-1-(3-methoxy-benzyl)-isoquinoline-4-carbaldehyde

생성물 1

HCID 220482916-Butoxy-7-methoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carbaldehyde수율 63%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
120 °C

실험 절차

To a stirred solution of 6-butoxy-7-methoxy-1-(3-methoxy-benzyl)-isoquinoline-4-carbaldehyde (200 mg, 0.53 mmol) in acetic acid (5 mL) was added selenium dioxide (175 mg, 1.58 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-butoxy-7-methoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carbaldehyde as a yellow solid (131 mg, 63% 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-1faf942937da41df9e9d3e77f86e0cb8
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067529B2

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