Potassium Carbonate → {2-[3-(Quinolin-2-ylmethoxy)phenoxymethyl]-6-methylphenoxy}acetonitrile

HRID 892166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 892166
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1.Br[CH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:23]=1[O:24][CH2:25][C:26]#[N:27].C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[O:19][CH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:23]=1[O:24][CH2:25][C:26]#[N:27]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 10988736Phenol, 3-(2-quinolinylmethoxy)-HCID 222414892-Cyanomethoxy-3-methylbenzyl bromide

Produkt 1

HCID 22241372{2-[3-(Quinolin-2-ylmethoxy)phenoxymethyl]-6-methylphenoxy}acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

3-(Quinolin-2-ylmethoxy)-phenol (1.3 g, 5.4 mmol, example 3), (2-bromomethyl-6-methyl-phenoxy)-acetonitrile (1.56 g, 6.5 mmol, example 24), tetrabutylammonium iodide (99 mg, 0.27 mmol) and potassium carbonate (0.45 g, 3.3 mmol) are refluxed in acetone (20 mL) for 16 h. The reaction is filtered, washed with dichloromethane, concentrated and purified by column chromatography (silica, 1% ether in dichloromethane) to provide the title compound. MS (ESI) 411 (M+H)+.

Aufarbeitung

  1. filtrationThe reaction is filtered
  2. washwashed with dichloromethane
  3. concentrationconcentrated
  4. custompurified by column chromatography (silica, 1% ether in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-c8707e5628f84cdfaff56bb4111b810f
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07005440B1

Notizen zur Reaktion

Wird geladen…