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Dimethylformamide → 6-benzyloxy-4-formyl-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester

HRID 1833139
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1833139
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[CH2:11]([O:13][C:14]([N:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][C:20]([O:34][CH3:35])=[C:21]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:22]=2)[CH:17]1[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH3:44])[CH:38]=1)=[O:15])[CH3:12].C([O-])(=O)C.[K+]>ClCCl.O.C(OCC)(=O)C.CCCCCC>[CH2:11]([O:13][C:14]([N:16]1[CH:25]=[C:24]([CH:3]=[O:4])[C:23]2[C:18](=[CH:19][C:20]([O:34][CH3:35])=[C:21]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:22]=2)[CH:17]1[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH3:44])[CH:38]=1)=[O:15])[CH3:12]
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Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517044Potassium AcetateHCID 210349386-benzyloxy-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester

Produkt 1

HCID 210349396-benzyloxy-4-formyl-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl esterAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittel2×HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

To anhydrous N,N-dimethylformamide (0.078 mL, 1.02 mmol) at 0° C. was added phosphorus oxychloride (0.042 mL, 0.44 mmol) dropwise. The mixture was warmed to room temperature and stirred for 30 minutes. The mixture was cooled in an ice-bath, and 6-benzyloxy-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester (156 mg, 0.34 mmol) in dichloromethane (3 mL) was added dropwise. After addition was complete, the mixture was heated on an oil bath for 4 hrs at 80° C. The mixture was cooled to 0° C. and a solution of potassium acetate (154 mg, 1.56 mmol) in water (2 mL) was added slowly. The mixture was then heated at 80° C. for 20 minutes. The mixture was cooled, poured into water and diluted with dichloromethane (60 mL). The organic layer was washed water (2×20 mL), 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, 20% ethyl acetate/hexane,) afforded 6-benzyloxy-4-formyl-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester as a colorless oil (85 mg, 52% yield).

Aufarbeitung

  1. temperatureThe mixture was cooled in an ice-bath
  2. additionAfter addition
  3. temperaturethe mixture was heated on an oil bath for 4 hrs at 80° C
  4. temperatureThe mixture was cooled to 0° C.
  5. temperatureThe mixture was then heated at 80° C. for 20 minutes
  6. temperatureThe mixture was cooled
  7. washThe organic layer was washed water (2×20 mL), saturated aqueous sodium bicarbonate solution (20 mL), saturated aqueous sodium chloride solution (20 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto afford a crude oil

Quellen und Nachweise

ORD-Eintrag
ord-6540dcf27e2e4168b50c9718b7962b98
Quelldatensatz
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07067529B2

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