Picolinic acid → Ethyl 2-(5-chloropyridin-2-YL)acetate

HRID 82175

반응식

HRID 82175 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][N:9]=1.C(OCC)(=O)[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].N1C=CC=CC=1C(O)=O>O1CCOCC1.[Cu-]=O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:9][CH:10]=1

참가 물질

7

반응물 4

HCID 1018Picolinic acidHCID 7761Diethyl MalonateHCID 10796Cesium carbonateHCID 8170982-Bromo-5-chloropyridine

생성물 1

HCID 55263201Ethyl 2-(5-chloropyridin-2-YL)acetate수율 54%

시약·촉매·용매 2

HCID 178419072HCID 178419072, 화합물촉매HCID 312751,4-Dioxane용매

반응 조건

온도
130 °C

실험 절차

Cesium carbonate (71 g, 218 mmol) was added to 2-bromo-5-chloropyridine (14 g, 73 mmol) and diethyl malonate (22 mL, 145 mmol) in dry 1,4-dioxane (280 mL) and the solution was degassed with argon for 30 minutes. Then copper (I) oxide (2.8 g, 14.55 mmol) and picolinic acid (3.6 g, 29 mmol) were added and the mixture was stirred in a sealed vessel at 130° C. for 24 hours. The mixture was cooled to room temperature, quenched with water (100 mL) and extracted with EtOAc (3×100 ml). The organic extracts were washed with water (200 mL), brine (200 mL), dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc:Hexane 92:8) to afford the title compound as a yellow oil in 54% yield, 8.0 g.

후처리

  1. customthe solution was degassed with argon for 30 minutes
  2. temperatureThe mixture was cooled to room temperature
  3. customquenched with water (100 mL)
  4. extractionextracted with EtOAc (3×100 ml)
  5. washThe organic extracts were washed with water (200 mL), brine (200 mL)
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel (EtOAc:Hexane 92:8)

출처 및 근거

ORD 기록
ord-81ff80f730b34595aaf541e143b1fa47
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

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