Toluene → ethyl 1-cyclopropyl-3-methyl-1H-pyrazole-5-carboxylate

HRID 873824노트

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HRID 873824 반응식
[CH:1]1([NH:4][NH2:5])[CH2:3][CH2:2]1.[C:6]([O:12][CH2:13][CH3:14])(=O)[O:7]COC.[C:15]1(C)[CH:20]=CC=[CH:17][CH:16]=1>CCO>[CH:1]1([N:4]2[C:20]([C:6]([O:12][CH2:13][CH3:14])=[O:7])=[CH:15][C:16]([CH3:17])=[N:5]2)[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 1140TolueneHCID 19594968CyclopropylhydrazineHCID 23565620Ethyl methoxymethyl carbonate

생성물 1

HCID 117702822ethyl 1-cyclopropyl-3-methyl-1H-pyrazole-5-carboxylate수율 34%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
100 °C

실험 절차

To a stirred solution of cyclopropylhydrazine (Step 17.2) (4.90 g, 45.1 mmol) in toluene (30 mL) and EtOH (30 mL) was added ethyl 2,4-dioxavalerate (6.34 mL, 45.1 mmol). The reaction mixture was stirred for 1 hr at 100° C., quenched with a saturated aq. NaHCO3 solution, and extracted with EtOAc. The combined organic layers were washed with a saturated aq. NaHCO3 solution, dried over Na2SO4 and evaporated. The crude material was purified by silica gel column chromatography (hexane/EtOAc 2.5-30%) to afford the title product (3.01 g, 15.50 mmol, 34% yield). tR: 4.70 min (HPLC 1); tR: 1.01 min (LC-MS 2); ESI-MS: 195 [M+H]+ (LC-MS 2); Rf=0.33 (hexane/EtOAc 9:1).

후처리

  1. customquenched with a saturated aq. NaHCO3 solution
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with a saturated aq. NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe crude material was purified by silica gel column chromatography (hexane/EtOAc 2.5-30%)

출처 및 근거

ORD 기록
ord-29e6dac029ce489eb150e45fbea933b4
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975417B2

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