Cesium carbonate → 6-(2-Methyl-2-propenyloxy)-2-(3-phenylpropyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline

HRID 1741705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1741705
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][CH2:5]2.Cl[CH2:23][C:24]([CH3:26])=[CH2:25].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[CH3:25][C:24](=[CH2:23])[CH2:26][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][CH2:5]2

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 112413-Chloro-2-methyl-1-propeneHCID 189639836-Hydroxy-2-(3-phenylpropyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 189639656-(2-Methyl-2-propenyloxy)-2-(3-phenylpropyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 6-hydroxy-2-(3-phenylpropyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline (1.5 g, 5.34 mmol) in acetone (80 ml) is added 3-chloro-2-methylpropene (8 ml, 8.01 mmol), Cs2CO3 and a catalytic amount of KI. The reaction is then refluxed for 24 hours. After this time the reaction mixture is cooled to ambient temperature and filtered. The filter cake is washed with acetone (3×50 ml) and the combined organics concentrated in vacuo. The residue is chromatographed (silica gel, 1:4 EtOAc/hexane) to give 6-(2-methyl-2-propenyloxy)-2-(3-phenylpropyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Aufarbeitung

  1. temperatureThe reaction is then refluxed for 24 hours
  2. filtrationfiltered
  3. washThe filter cake is washed with acetone (3×50 ml)
  4. concentrationthe combined organics concentrated in vacuo
  5. customThe residue is chromatographed (silica gel, 1:4 EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c74838b2ce714eeea8ee9ac081d9cd28
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05334600

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