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

HRID 2102257
ノート
印刷プレビュー

反応式

HRID 2102257 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

HCID 178469772Ethyl 3-hydroxy-1-isopropylpyrazole-4-carboxylate収率 35.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒
HCID 57417360Sodium chloride; water溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7970bb2cc9344010b16fadce33b0932b
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07576064B2

反応ノート

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