Acetic Acid → ethyl 5-(2-hydroxy-2-methylpropyl)-1-propyl-1H-pyrazole-3-carboxylate

HRID 1095372

반응식

HRID 1095372 반응식
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[Na+].[C:7]([O:14][CH2:15][CH3:16])(=[O:13])[C:8](OCC)=O.[C:17](O)(=O)[CH3:18].C(O)(=O)C(O)=O.[CH2:27]([NH:30][NH2:31])[CH2:28][CH3:29]>C(O)C>[OH:4][C:2]([CH3:5])([CH3:3])[CH2:1][C:17]1[N:30]([CH2:27][CH2:28][CH3:29])[N:31]=[C:8]([C:7]([O:14][CH2:15][CH3:16])=[O:13])[CH:18]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7268Diethyl OxalateHCID 96079Hydrazine, propyl-, ethanedioate (1:1)HCID 23676156Sodium t-butoxide

생성물 1

HCID 66781950ethyl 5-(2-hydroxy-2-methylpropyl)-1-propyl-1H-pyrazole-3-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of sodium tert-butoxide dissolved in ethanol (71 mL) was added diethyl oxalate (16.1 g, 110 mmol) followed by the material obtained in Part A (18.8 g, 100 mmol). The reaction was stirred 30 minutes at ambient temperature before cooling to 0° C. and adding acetic acid (100 mL) and propylhydrazine oxalate (16.4 g, 100 mmol). The reaction was allowed to warm to ambient temperature and stirred for 19 hours. The solvent was removed under reduced pressure. The resulting brown oil was purified by automated flash chromatography (AnaLogix, eluting with a gradient of 50-75% ethyl acetate in hexanes) to provide 9.6 g of ethyl 5-(2-hydroxy-2-methylpropyl)-1-propyl-1H-pyrazole-3-carboxylate as a yellow oil.

후처리

  1. customobtained in Part A (18.8 g, 100 mmol)
  2. temperaturebefore cooling to 0° C.
  3. temperatureto warm to ambient temperature
  4. stirringstirred for 19 hours
  5. customThe solvent was removed under reduced pressure
  6. customThe resulting brown oil was purified by automated flash chromatography (AnaLogix
  7. washeluting with a gradient of 50-75% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-0beb1909aaac4e39a96bf49c09c5c581
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138173B2

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