Potassium Iodide → 2-(4'-Fluoro-4-biphenylylmethyl)-6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

HRID 2226968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226968
[CH3:1][O:2][CH:3]([O:17][CH3:18])[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[NH:11][CH2:10][CH2:9]2.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32]Br)=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.[H-].[Na+].[I-].[K+]>CN(C=O)C.O>[F:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][N:11]3[CH2:10][CH2:9][C:8]4[C:13](=[CH:14][CH:15]=[C:6]([O:5][CH2:4][CH:3]([O:2][CH3:1])[O:17][CH3:18])[CH:7]=4)[C:12]3=[O:16])=[CH:28][CH:27]=2)=[CH:24][CH:25]=1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 189638634-(Bromomethyl)-4'-fluoro-1,1'-biphenylHCID 189638836-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 189639412-(4'-Fluoro-4-biphenylylmethyl)-6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline (5.79 g, 23.05 mmol) and 4'-fluoro-4-biphenylylmethyl bromide (9.16 g, 34.57 mmol), in DMF (100 ml) is added sodium hydride (1.1 g, 27.5 mmol) and a catalytic amount of potassium iodide. The reaction mixture is stirred for 2 hours at room temperature and is subsequently diluted with H2O (500 ml). The mixture is then extracted with EtOAc (2×300 ml). The combined EtOAc portions are washed with saturated NaCl solution (600 ml), dried over MgSO4, and concentrated in vacuo and washed with hexanes to yield the acetal, 2-(4'-fluoro-4-biphenylylmethyl)-6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Aufarbeitung

  1. extractionThe mixture is then extracted with EtOAc (2×300 ml)
  2. washThe combined EtOAc portions are washed with saturated NaCl solution (600 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. washwashed with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-23547bdad43946658ed2364844952d8c
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05350761

Notizen zur Reaktion

Wird geladen…