N,N'-二甲基乙二胺 → 1-(5,6-Diphenyl-pyridin-2-yl)-ethanone

HRID 12553

反应方程式

HRID 12553 反应方程式
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:19]([O:21]CC)=O)=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24]NCCNC.C[Al](C)C>C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:19](=[O:21])[CH3:24])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参与物

5

反应物 3

HCID 8070N,N'-二甲基乙二胺HCID 14789610Ethyl 5,6-diphenylpyridine-2-carboxylate2 次HCID 16682925三甲基铝

产物 1

HCID 593388261-(5,6-Diphenyl-pyridin-2-yl)-ethanone

试剂、催化剂与溶剂 1

HCID 1140甲苯溶剂

反应条件

温度
112 °C

实验过程

General Procedure O. To a solution of ethyl 5,6-diphenylpyridine-2-carboxylate (Compound 21, 246 mg, 0.81 mmol) in toluene (5 ml) was added N,N′-dimethylethylenediamine (DMEDA, 78.7 mg, 0.89 mmol) and trimethylaluminum (1.2 ml, 2.44 mmol, 2 M in toluene) dropwise under argon at room temperature. After the mixture was refluxed at 112° C. for 2.5 hours, it was quenched with water, and the products were extracted with ethyl acetate. The combined organic layers were washed with brine, and dried over Na2SO4. The filtered solvents were concentrated in vacuo, and the residue was purified by silica gel chromatography (15% ethyl acetate in hexane) to give title compound as a yellow solid.

后处理

  1. customit was quenched with water
  2. extractionthe products were extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe filtered solvents were concentrated in vacuo
  6. customthe residue was purified by silica gel chromatography (15% ethyl acetate in hexane)

来源与证据

ORD记录
ord-a2896fc6ab234e46af24b98823239a8b
来源数据集
uspto-grants-2010_06
专利号
US07728014B2

关联笔记

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