莫诺苯宗 → 3-(4-Benzyloxy-phenoxy)-pyridine

HRID 1909774

反应方程式

HRID 1909774 反应方程式
[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

参与物

9

反应物 4

HCID 7638莫诺苯宗HCID 8150二乙二醇二甲醚HCID 10796碳酸氢铯HCID 707143-碘吡啶

产物 1

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

试剂、催化剂与溶剂 4

HCID 24350碘化亚铜催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8857乙酸乙酯溶剂HCID 312751,4-二氧六环溶剂

实验过程

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%).

后处理

  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

来源与证据

ORD记录
ord-f25cd57d69554f58ab2905fc224187d6
来源数据集
uspto-grants-2013_12
专利号
US08598359B2

关联笔记

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