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

HRID 1833151ノート

反応式

HRID 1833151 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1faf942937da41df9e9d3e77f86e0cb8
出典データセット
uspto-grants-2006_06
特許番号
US07067529B2

反応ノート

読み込み中…