甲苯 → HCID 22600462，化合物

HRID 1784150笔记

反应方程式

HRID 1784150 反应方程式
Cl[C:2]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[C:4](=[O:10])[CH:3]=1.[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16][C:17]1[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20].C(N(C(C)C)CC)(C)C.C1(C)C=CC=CC=1>[Cl-].[Cl-].[Zn+2].ClCCl>[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16][C:17]1[C:18]([C:19]([O:21][C:2]2[CH:8]3[CH2:9][CH:5]([CH2:6][CH2:7]3)[C:4](=[O:10])[CH:3]=2)=[O:20])=[CH:22][CH:23]=[C:24]([C:26]([F:29])([F:27])[F:28])[N:25]=1

参与物

7

反应物 4

HCID 1140甲苯HCID 81531N,N-二异丙基乙胺HCID 11334953BICYCLOPYRONE METABOLITE BHCID 57591516HCID 57591516，化合物

产物 1

HCID 22600462HCID 22600462，化合物

试剂、催化剂与溶剂 2

HCID 3007855氯化锌催化剂HCID 6344二氯甲烷溶剂

实验过程

A mixture of 200 mg (1.15 mmol) of 4-chlorobicyclo[3.2.1]oct-3-en-2-one, (Preparation Example P2) 16 mg (0.12 mmol) of ZnCl2, 324 mg (1.15 mmol) of 2-methoxyethoxymethyl-6 -trifluoromethylnicotinic acid, 166 mg (1.27 mmol) of diisopropylethylamine and 5 ml of toluene is stirred under a nitrogen atmosphere at room temperature until a clear brown solution having a white sediment is formed. The reaction mixture is then maintained under moderate reflux for 26 hours in an oil bath, with stirring. The reaction mixture is then cooled to ambient temperature and 30 ml of dichloromethane are added. The solution is then washed twice with water (20 ml each time) and then twice with 0.1M hydrochloric acid (20 ml each time) and again twice with water (15 ml each time). After drying the organic solution using magnesium sulfate and concentrating in vacuo, 284 mg of 4-(2-methoxyethoxymethyl-6-trifluoromethyl-pyridin-3-ylcarbonyloxy)-bicyclo[3.2.1]oct-3-en-2-one are obtained in the form of a brown oil.

后处理

  1. customis formed
  2. temperatureThe reaction mixture is then maintained
  3. temperatureunder moderate reflux for 26 hours in an oil bath
  4. stirringwith stirring
  5. temperatureThe reaction mixture is then cooled to ambient temperature
  6. washThe solution is then washed twice with water (20 ml each time)
  7. customAfter drying the organic solution
  8. concentrationconcentrating in vacuo, 284 mg of 4-(2-methoxyethoxymethyl-6-trifluoromethyl-pyridin-3-ylcarbonyloxy)-bicyclo[3.2.1]oct-3-en-2-one
  9. customare obtained in the form of a brown oil

来源与证据

ORD记录
ord-e08e1cbc6beb424492820e89b8e50368
来源数据集
uspto-grants-2009_03
专利号
US07501544B2

反应笔记

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