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Dimethylformamide → Methyl 5-cyano-[1,1'-biphenyl]-3-carboxylate

HRID 1096951
ノート
印刷プレビュー

反応式

HRID 1096951 の反応式
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]([C:19]([O:21][CH3:22])=[O:20])[CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1)(=O)=O.[CH3:25][N:26](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:25]([C:7]1[CH:8]=[C:9]([C:19]([O:21][CH3:22])=[O:20])[CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1)#[N:26]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 57930914Methyl 5-{[(trifluoromethyl)sulfonyl]oxy}biphenyl-3-carboxylate

生成物 1

HCID 57346364Methyl 5-cyano-[1,1'-biphenyl]-3-carboxylate

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
90 °C

実験手順

Zinc cyanide (1.1 g) and Pd(PPh3)4 (281 mg) were added to a DMF (45 mL) solution of methyl 5-{[(trifluoromethyl)sulfonyl]oxy}biphenyl-3-carboxylate (1.68 g), and stirred at 90° C. for 1 hour and 30 minutes. The reaction liquid was filtered through Celite, the solvent was partly evaporated away, and the residue was diluted with ethyl acetate, aqueous ammonia was added to it, and the solution was extracted with ethyl acetate. The organic layer was washed with water and saturated saline water, dried with anhydrous sodium sulfate, filtered, and the solvent was evaporated away. The residue was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a white powder.

後処理

  1. customThe reaction liquid
  2. filtrationwas filtered through Celite
  3. customthe solvent was partly evaporated away
  4. additionthe residue was diluted with ethyl acetate, aqueous ammonia
  5. additionwas added to it
  6. extractionthe solution was extracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated saline water
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated away
  11. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-00e8522431594b2b8ce1b931a8ea608a
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08138197B2

反応ノート

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