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

HRID 1833161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1833161
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 220483816-Cyclopentyloxy-7-methoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carbaldehydeAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2c3616fb8492406885dfec3dacb34322
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067529B2

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