聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 5-苄氧基吲哚啉

HRID 49492

反应方程式

HRID 49492 反应方程式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH3-]C#N.[Na+].O.[OH-].[K+]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH2:13][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 146245-苄氧基吲哚HCID 14797氢氧化钾HCID 5003444氰基硼氢化钠

产物 1

HCID 167948815-苄氧基吲哚啉收率 89.2%

试剂、催化剂与溶剂 1

HCID 176醋酸溶剂

实验过程

In analogy to the method described by Gordon W. Gribble, Joseph H. Hoffmann Synthesis 1977, 859-860, the following reaction was performed. To a precooled solution of 22.3 g (0.1 mol) 5-benzyloxyindole in 270 ml acetic acid, 19 g (0.3 mol) NaCNBH3 were added. The solution was stirred at RT for 2 h, the volume was reduced to one third and poured into 300 ml water. KOH was added under cooling and the solution was extracted with ether. The combined organic phases were washed with water, dried over Na2SO4 and evaporated to yield 20.1 g (89%) 5-Benzyloxy-2,3-dihydro-1H-indole as colorless oil, MS: 225 (M).

后处理

  1. customHoffmann Synthesis 1977, 859-860
  2. customthe following reaction
  3. temperatureunder cooling
  4. extractionthe solution was extracted with ether
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated

来源与证据

ORD记录
ord-bd86c4538ce548e0b9203acfa8be0660
来源数据集
uspto-grants-2004_03
专利号
US06706751B2

关联笔记

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