3,4-Dimethylpyridine → 1-(2-Furyl)-2-(3-methylpyridin-4-yl)ethanone

HRID 337528

反応式

HRID 337528 の反応式
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](OCC)=[O:15].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[Cl-].[NH4+]>C1COCC1>[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](=[O:15])[CH2:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH3:1]

参加物

6

反応物 4

HCID 114173,4-DimethylpyridineHCID 11980Ethyl 2-furoateHCID 25517Ammonium ChlorideHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 231444431-(2-Furyl)-2-(3-methylpyridin-4-yl)ethanone収率 83%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

3,4-Dimethylpyridine (2.25 mL, 20.0 mmol) and ethyl furan-2-carboxylate (5.02 mL, 40.0 mmol) were dissolved in THF (20 mL), and at 0° C., a 1.0 mol/L solution of lithium hexamethyldisilazide in THF (40.0 mL, 40.0 mmol) was added dropwise thereto, followed by stirring at room temperature for 1.5 hours. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was washed successively with a saturated aqueous solution of ammonium chloride and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:2) to afford 1-(2-furyl)-2-(3-methylpyridin-4-yl)ethanone (3.34 g, 16.6 mmol).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed successively with a saturated aqueous solution of ammonium chloride
  3. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:2)

出典と根拠

ORDレコード
ord-d70083a2bb214931a9c315615149e280
出典データセット
uspto-grants-2014_11
特許番号
US08889718B2

関連ノート

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