Water → 1,5-Dimethyl-3-ethoxycarbonylpyrazole

HRID 1825331

反応式

HRID 1825331 の反応式
O=[C:2]([CH2:8][C:9](=O)[CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:12][NH:13][NH2:14].C(OCC)(=O)C.O>C(O)(=O)C>[CH2:6]([O:5][C:3]([C:2]1[CH:8]=[C:9]([CH3:10])[N:13]([CH3:12])[N:14]=1)=[O:4])[CH3:7]

参加物

6

反応物 4

HCID 962WaterHCID 6061MethylhydrazineHCID 8857Ethyl AcetateHCID 69208Ethyl 2,4-dioxovalerate

生成物 1

HCID 1385771,5-Dimethyl-3-ethoxycarbonylpyrazole

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Ethyl 2,4-dioxovalerate (5.6 ml, 40 mM) was dissolved in glacial acetic acid (35 ml) before cooling the-reaction temperature to 8-10° C. Methylhydrazine (2.0 ml, 38 mM) was added dropwise so that the reaction temperature did not rise above 15° C. After stirring at room temperature for 90 minutes the reaction was poured into ethyl acetate and water. The organic phase was washed with saturated sodium bicarbonate solution, water and brine before drying (MgSO4). Purification was accomplished was by chromatography on silica gel (10×4.5 cm) loading in dichloromethane and eluting with 50% ethyl acetate in hexane. Evaporation of solvent gave the title compound as a coloured oil which crystallised on standing (4.69 g); υmax (CH2Cl2) 1717 and 1223 cm−1; δH (CDCl3) 1.39 (3H, t, J 7.13 Hz), 2.30 (3H, s), 3.85 (3H, s), 4.39 (2H, q, J 7.21 Hz), 6.57 (1H, s); E.I. m/e 168 (25%).

後処理

  1. temperaturebefore cooling
  2. customthe-reaction temperature to 8-10° C
  3. customdid not rise above 15° C
  4. washThe organic phase was washed with saturated sodium bicarbonate solution, water and brine
  5. dry with materialbefore drying (MgSO4)
  6. customPurification
  7. washeluting with 50% ethyl acetate in hexane
  8. customEvaporation of solvent

出典と根拠

ORDレコード
ord-58464fc4319b4dd78e46328d58954e3f
出典データセット
uspto-grants-2006_05
特許番号
US07045619B2

関連ノート

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