Methyl iodide → Methyl 1,4-dimethyl-1H-pyrazole-5-carboxylate

HRID 244615

反応式

HRID 244615 の反応式
[CH3:1][C:2]1[CH:3]=[N:4][NH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[C:11](=O)([O-])[O-].[Cs+].[Cs+].CI>C(#N)C.O.C(Cl)Cl>[CH3:11][N:5]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:2]([CH3:1])[CH:3]=[N:4]1

参加物

7

反応物 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 3467807Methyl 4-methyl-1H-pyrazole-3-carboxylate

生成物 1

HCID 20718564Methyl 1,4-dimethyl-1H-pyrazole-5-carboxylate収率 31.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

Methyl 4-methyl-1H-pyrazole-5-carboxylate (0.5 g) and cesium carbonate (1.16 g) were dissolved in acetonitrile (10 ml). Methyl iodide (0.25 ml) was added and the mixture stirred at RT for 16 h. The reaction mixture was diluted with water (20 ml) and DCM (20 ml) and separated using a hydrophobic frit. The aqueous layer was extracted with DCM (2×20 ml) using a hydrophobic frit. The solvent was removed in vacuo and the residue was purified by flash chromatography eluting with a gradient of 0-100% ethyl acetate in cyclohexane to give the title compound (0.172 g) as a colourless oil.

後処理

  1. customseparated
  2. extractionThe aqueous layer was extracted with DCM (2×20 ml)
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash chromatography
  5. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane

出典と根拠

ORDレコード
ord-366bb9393deb4a7ebef3a57a10006196
出典データセット
uspto-grants-2014_02
特許番号
US08658635B2

関連ノート

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