Ethyl Acetate → alpha-(1,1-Dimethylethyl)-3-pyridinemethanol

HRID 1186328ノート

反応式

HRID 1186328 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.[C:9]([Li])([CH3:12])([CH3:11])[CH3:10].[Cl-].[NH4+].C(OCC)(=O)C>O1CCCC1.CCCCC>[CH3:10][C:9]([CH3:12])([CH3:11])[CH:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[OH:8]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 103713-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 178418306HCID 178418306、化合物

生成物 1

HCID 322666alpha-(1,1-Dimethylethyl)-3-pyridinemethanol収率 18%

試薬・触媒・溶媒 2

HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

3-Pyridinecarboxaldehyde (200 μL, 2.12 mmol) was dissolved in tetrahydrofuran (5.0 mL). To this, tert-butyllithium (a 1.46 mol/L solution in pentane, 4.37 mL, 6.36 mmol) was added dropwise under a nitrogen atmosphere at 0° C. and the mixture was stirred at the same temperature for 1. Then, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=9/1, hexane/ethyl acetate=1/1) to give 3-(2,2-dimethyl-1-hydroxypropyl)pyridine (Compound CG) (64.0 mg, yield: 18%).

後処理

  1. washby washing with brine
  2. dry with materialdrying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform/methanol=9/1, hexane/ethyl acetate=1/1)

出典と根拠

ORDレコード
ord-800644b7ff474971acd8d93cf1b79195
出典データセット
uspto-grants-2014_03
特許番号
US08673908B2

反応ノート

読み込み中…