Bromobenzene → [Diphenyl(4-pyridyl)]methanol

HRID 80305ノート

反応式

HRID 80305 の反応式
[Mg].Br[C:3]1C=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+].[O:25]1CCC[CH2:26]1>>[C:10]1([C:9]2[C:19]([C:18]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:20][CH:21]=[CH:22][C:17]=2[CH2:26][OH:25])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

参加物

6

反応物 5

HCID 7961BromobenzeneHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 267314-BenzoylpyridineHCID 5462224Magnesium

生成物 1

HCID 67428383[Diphenyl(4-pyridyl)]methanol収率 97%

実験手順

A Grignard reagent was prepared from magnesium (0.21 g, 8.64 mmol) (Wako Pure Chemical Industries, Ltd.) and bromobenzene (1.35 g, 8.60 mmol) (Wako Pure Chemical Industries, Ltd.). 4-Benzoylpyridine (0.52 g, 28.4 mmol) (Wako Pure Chemical Industries, Ltd.) was dissolved in tetrahydrofuran (10 mL) (Wako Pure Chemical Industries, Ltd.), and the Grignard reagent was added dropwise, followed by stirring at room temperature for 5 hours. A saturated aqueous solution of ammonium chloride (Wako Pure Chemical Industries, Ltd.) was added to the reaction solution, and mixture was extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.). The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.) as an eluent), to thereby obtain the title compound (0.72 g, 97% yield).

後処理

  1. extractionwas extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
  2. dry with materialThe organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  3. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-5f4e81eb6c9d44cca72f66321c991c50
出典データセット
uspto-grants-2014_09
特許番号
US08846012B2

反応ノート

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