Monobenzone → 3-(4-Benzyloxy-phenoxy)-pyridine

HRID 1909774

Reaktionsgleichung

Reaktionsgleichung von HRID 1909774
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].I[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1.COCCOCCOC>O1CCOCC1.[Cu]I.O.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

9

Edukt 4

HCID 7638MonobenzoneHCID 8150DiglymeHCID 10796Cesium carbonateHCID 707143-Iodopyridine

Produkt 1

HCID 689991853-(4-Benzyloxy-phenoxy)-pyridineAusbeute 26,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of p-benzyloxyphenol (550 mg, 2.754 mmol), Cs2CO3 (1.795 g, 5.509 mmol), 3-iodo pyridine (850 mg, 4.14 mmol) in anhydrous dioxane (15 ml) under N2 was added diglyme (38.42 mg, 0.275 mmol). After stirring for 10 min, CuI (19.38 mg, 0.102 mmol) was added and the reaction mixture was kept in a shaker at 85° C. overnight. The mixture was poured into EtOAc and water, the organic layer was dried over Na2SO4, and concentrated. Silica gel flash chromatography using EtOAc/Hexane gave the title compound (200 mg, 17%).

Aufarbeitung

  1. waitthe reaction mixture was kept in a shaker at 85° C. overnight
  2. dry with materialthe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f25cd57d69554f58ab2905fc224187d6
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598359B2

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