N,N'-Dimethylethylenediamine → 1-(5,6-Diphenyl-pyridin-2-yl)-ethanone

HRID 12553

反応式

HRID 12553 の反応式
[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

参加物

5

反応物 3

HCID 8070N,N'-DimethylethylenediamineHCID 14789610Ethyl 5,6-diphenylpyridine-2-carboxylate2 回HCID 16682925Trimethylaluminum

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
112 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a2896fc6ab234e46af24b98823239a8b
出典データセット
uspto-grants-2010_06
特許番号
US07728014B2

関連ノート

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