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Hydrochloric Acid → Ethyl 3-hydroxy-1-isopropylpyrazole-4-carboxylate

HRID 2102257
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HRID 2102257 반응식
C[O-].[Na+].CCO[CH:7]=[C:8]([C:14]([O:16]CC)=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[CH:19]([NH:22][NH2:23])([CH3:21])[CH3:20].Cl>C(O)C.[Cl-].[Na+].O>[OH:16][C:14]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][N:22]([CH:19]([CH3:21])[CH3:20])[N:23]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 527891-IsopropylhydrazineHCID 10942334Sodium Methoxide

생성물 1

HCID 178469772Ethyl 3-hydroxy-1-isopropylpyrazole-4-carboxylate수율 35.1%

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 57417360Sodium chloride; water용매

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온도
80 °C

실험 절차

To a solution of sodium methoxide (23 g) in ethanol (150 mL) were added diethyl ethoxymethylene malonate (32.7 g) and isopropyl hydrazine (11.2 g) at room temperature. The mixture was stirred at 80° C. for 4 hours and stirred at 100° C. for another 2 hours. The reaction mixture was poured into 2 mol/L hydrochloric acid (300 mL). After the mixture was diluted with brine, the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5) to give 10.5 g of the title compound.

후처리

  1. stirringstirred at 100° C. for another 2 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5)

출처 및 근거

ORD 기록
ord-7970bb2cc9344010b16fadce33b0932b
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07576064B2

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