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

HRID 577149ノート

反応式

HRID 577149 の反応式
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]

参加物

6

反応物 5

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

生成物 1

HCID 59589505Ethyl 2,4-diethylpyridine-3-carboxylate収率 46%

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b8727495d6ba423499299407a0bf4e29
出典データセット
uspto-grants-2015_05
特許番号
US09040538B2

反応ノート

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