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

HRID 1909774

Reaction equation

HRID 1909774 reaction equation
[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

Participants

9

Reactant 4

HCID 7638MonobenzoneHCID 8150DiglymeHCID 10796Cesium carbonateHCID 707143-Iodopyridine

Product 1

HCID 689991853-(4-Benzyloxy-phenoxy)-pyridineYield 26.2%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-f25cd57d69554f58ab2905fc224187d6
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Linked notes

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