聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → (+/-)-2-Propionyl-2-azabicyclo[2.2.1]hept-5-en-3-one

HRID 369495笔记

反应方程式

HRID 369495 反应方程式
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[C:3](=[O:8])[NH:2]2.N1C=CC=CC=1.[C:15](Cl)(=[O:18])[CH2:16][CH3:17].O>C(#N)C>[C:15]([N:2]1[C:3](=[O:8])[CH:4]2[CH2:7][CH:1]1[CH:6]=[CH:5]2)(=[O:18])[CH2:16][CH3:17]

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 1049吡啶HCID 62324丙酰氯HCID 5486782-氮杂双环[2.2.1]庚-5-烯-3-酮

产物 1

HCID 22673281(+/-)-2-Propionyl-2-azabicyclo[2.2.1]hept-5-en-3-one收率 81.6%

试剂、催化剂与溶剂 1

HCID 6342乙腈溶剂

实验过程

47 g of (±)-2-azabicyclo[2.2.1]hept-5-en-3-one were dissolved in acetonitrile (325 ml) and pyridine (41 ml) under nitrogen. At 12° C., 43.9 g of propionyl chloride were added dropwise over the course of 1 h. The reaction was then stirred at room temperature for 5 h. 145 ml of water were added to the mixture, and the acetonitrile was evaporated off in vacuo. The aqueous phase was extracted 3 times with 115 ml of ethyl acetate. The combined organic phases were washed with 1N HCl (140 ml), saturated NaHCO3 (40 ml) and NaCl (40 ml) solutions, dried with sodium sulphate and completely evaporated. The residue was purified by distillation. 55.8 g of title compound were obtained and solidified on leaving to stand. The yield was 81.6%.

后处理

  1. customthe acetonitrile was evaporated off in vacuo
  2. extractionThe aqueous phase was extracted 3 times with 115 ml of ethyl acetate
  3. washThe combined organic phases were washed with 1N HCl (140 ml), saturated NaHCO3 (40 ml) and NaCl (40 ml) solutions
  4. dry with materialdried with sodium sulphate
  5. customcompletely evaporated
  6. distillationThe residue was purified by distillation

来源与证据

ORD记录
ord-ec3cceb244724489a1b30918c61d8747
来源数据集
uspto-grants-2000_10
专利号
US06137007

反应笔记

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