Cesium carbonate → 6-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

HRID 257069

Reaktionsgleichung

Reaktionsgleichung von HRID 257069
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2.[I-].[Cs+].[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18]Br.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cl-].[Na+].O>[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 24601Cesium iodideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 159083146-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

Produkt 1

HCID 189638836-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 6-hydroxy-1-oxo-1,2,3,4-tetrahydroisoquinoline (25 g, 15.3 mmol), CsI (4 g, 15.3 mmol) and bromoacetaldehyde dimethyl acetal (40 ml, 338 mmol) in DMF (600 ml) is added Cs2CO3 (137.5 g, 460 mmol). The reaction mixture is heated at 60° overnight. After this time, the reaction is poured into 1 liter brine and the resulting suspension is extracted with EtOAc (4×400 ml). The combined EtOAc extracts are dried over MgSO4 and concentrated in vacuo. The residue is washed with Et2O to yield 6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline as a crystalline solid.

Aufarbeitung

  1. temperatureThe reaction mixture is heated at 60° overnight
  2. extractionthe resulting suspension is extracted with EtOAc (4×400 ml)
  3. dry with materialThe combined EtOAc extracts are dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. washThe residue is washed with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-1742ff794edb415bb609e30f4ecef1d1
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05260316

Verknüpfte Notizen

Wird geladen…