Water → 1,5-Dimethyl-3-ethoxycarbonylpyrazole

HRID 1825331

반응식

HRID 1825331 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 1385771,5-Dimethyl-3-ethoxycarbonylpyrazole

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-58464fc4319b4dd78e46328d58954e3f
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07045619B2

연결된 노트

불러오는 중…