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Isopropyl iodide → Ethyl 1-(1-methylethyl)-1H-pyrazole-5-carboxylate

HRID 244655
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HRID 244655 반응식
[NH:1]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:18]([CH3:20])[CH3:19]>C(#N)C>[CH3:19][CH:18]([N:1]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=[N:2]1)[CH3:20]
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참가 물질

5

반응물 3

HCID 6362Isopropyl iodide3회HCID 10796Cesium carbonateHCID 7147518Ethyl 1H-pyrazole-3-carboxylate

생성물 1

HCID 23005968Ethyl 1-(1-methylethyl)-1H-pyrazole-5-carboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
20 °C

실험 절차

To a solution of ethyl 1H-pyrazole-5-carboxylate (1 g) (for example, available form Bio-Farma) in acetonitrile (80 ml) was added cesium carbonate (2.32 g). 20 min later 2-iodopropane (0.714 ml) was added and the mixture stirred under nitrogen at 20° C. for 18 h. 2-Iodopropane (0.714 ml) was added and the mixture stirred under nitrogen at 20° C. for 5 h. Then further 2-iodopropane (0.714 ml) was added and the mixture was stirred at 20° C. for 18 h. The solvent was removed in vacuo and the residue was partitioned between water (30 ml) and DCM (30 ml). The aqueous phase was extracted with DCM (2×20 ml) and separated by hydrophobic frit. The combined organic layers were concentrated in vacuo. Purification of the residue by chromatography on silica gel (70 g silica), eluting with a gradient of 0-100% ethyl acetate in cyclohexane over 30 min gave the title compound (513 mg) as a yellow oil.

후처리

  1. stirringthe mixture stirred under nitrogen at 20° C. for 5 h
  2. stirringthe mixture was stirred at 20° C. for 18 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between water (30 ml) and DCM (30 ml)
  5. extractionThe aqueous phase was extracted with DCM (2×20 ml)
  6. customseparated by hydrophobic frit
  7. concentrationThe combined organic layers were concentrated in vacuo
  8. customPurification of the residue by chromatography on silica gel (70 g silica)
  9. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane over 30 min

출처 및 근거

ORD 기록
ord-1b621e9f15954dcdbce316bad1dafe54
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658635B2

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