Hydrochloric Acid → Ethyl 2,4-diethylpyridine-3-carboxylate

HRID 630192노트

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HRID 630192 반응식
Br[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH2:14]([Zn]CC)[CH3:15].O.Cl.O1CCO[CH2:23][CH2:22]1>>[CH2:14]([C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH2:22][CH3:23])[CH:5]=[CH:4][N:3]=1)[CH3:15]

참가 물질

6

반응물 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 312751,4-DioxaneHCID 59589350Ethyl 2-bromo-4-chloropyridine-3-carboxylateHCID 178418750HCID 178418750, 화합물

생성물 1

HCID 59589505Ethyl 2,4-diethylpyridine-3-carboxylate수율 46%

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온도
70 °C

실험 절차

Ethyl 2-bromo-4-chloropyridine-3-carboxylate (2.0 g, 7.6 mmol) was dissolved in anhydrous dioxane (55 mL). A solution of diethyl zinc (6.9 mL, 7.6 mmol, 1.1 M in toluene) was added dropwise, and then was added (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (83 mg, 113 μmol). The mixture was heated at 70° C. for 6 hours, and water followed by 1 N HCl was added. The mixture was extracted 3 times with ethyl acetate, and the combined organic phases were washed with brine and dried over sodium sulfate. After evaporation, the residue was dissolved in DCM and purified on silica gel using 0-20% hexane/ethyl acetate to afford ethyl 2,4-diethylpyridine-3-carboxylate (720 mg, 46% yield).

후처리

  1. additionwas added
  2. extractionThe mixture was extracted 3 times with ethyl acetate
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation
  6. dissolutionthe residue was dissolved in DCM
  7. custompurified on silica gel using 0-20% hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-cc541b2226a64e04bdd0c20aeb69ea6c
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315521B2

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