Hydrochloric Acid → Ethyl 4-chloro-2-ethylpyridine-3-carboxylate

HRID 577145ノート

反応式

HRID 577145 の反応式
Br[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([Cl:13])[CH:5]=[CH:4][N:3]=1.[CH2:14]([Zn]CC)[CH3:15].O.Cl>O1CCOCC1>[Cl:13][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH2:14][CH3:15])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

参加物

6

反応物 4

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

生成物 1

HCID 19902853Ethyl 4-chloro-2-ethylpyridine-3-carboxylate収率 63%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
40 °C

実験手順

Ethyl 2-bromo-4-chloropyridine-3-carboxylate (1.5 g, 5.7 mmol) was dissolved in anhydrous dioxane (45 mL). A solution of diethyl zinc (4.6 mL, 5.1 mmol, 1.1 M in toluene) was added dropwise, and then was added (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (62 mg, 85 μmol). The mixture was heated at 40° C. overnight, and then water plus 1 N HCl were added. The reaction mixture was extracted 3 times with ethyl acetate. The combined organic phase was washed with brine and dried over sodium sulfate. After evaporation, the residue was dissolved in DCM and purified on silica gel using 0-15% hexane/ethyl acetate to afford ethyl 4-chloro-2-ethylpyridine-3-carboxylate (687 mg, 57% yield).

後処理

  1. extractionThe reaction mixture was extracted 3 times with ethyl acetate
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter evaporation
  5. dissolutionthe residue was dissolved in DCM
  6. custompurified on silica gel using 0-15% hexane/ethyl acetate

出典と根拠

ORDレコード
ord-02314bdac21a459cae1c5d07b1787724
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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