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

HRID 1186328노트

반응식

HRID 1186328 반응식
[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]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 103713-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 178418306HCID 178418306, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 8003Pentane용매HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-800644b7ff474971acd8d93cf1b79195
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673908B2

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