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

HRID 1909774

反応式

HRID 1909774 の反応式
[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

参加物

9

反応物 4

HCID 7638MonobenzoneHCID 8150DiglymeHCID 10796Cesium carbonateHCID 707143-Iodopyridine

生成物 1

HCID 689991853-(4-Benzyloxy-phenoxy)-pyridine収率 26.2%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-f25cd57d69554f58ab2905fc224187d6
出典データセット
uspto-grants-2013_12
特許番号
US08598359B2

関連ノート

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