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Potassium Carbonate → Diethyl 1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-pyrazole-3,5-dicarboxylate

HRID 1158874
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HRID 1158874 반응식
[NH:1]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>C(#N)C.C(OCC)(=O)C>[Si:26]([O:25][CH2:24][CH2:23][N:1]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:2]1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 142184diethyl 1H-pyrazole-3,5-dicarboxylateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

생성물 1

HCID 68444496Diethyl 1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-pyrazole-3,5-dicarboxylate수율 100.1%

시약·촉매·용매 2

HCID 6342Acetonitrile용매
HCID 8857
Ethyl Acetate
용매

실험 절차

To a solution of diethyl 3,5-pyrazoledicarboxylate (2.17 g, 10 mmol) in acetonitrile (10 ml), under nitrogen, was added potassium carbonate (2.07 g, 15 mmol), and 2-bromoethoxy-t-butyldimethylsilane (2.90 g, 12 mmol). The mixture was stirred at reflux for 18 hr. It was then cooled to room temperature, diluted with ethyl acetate (20 ml), and filtered through Magnesol. The filter pad was eluted with 2×10 ml of ethyl acetate, and the combined filtrate was evaporated. The residue was dissolved in hexanes and passed through a column of silica gel (70 g). After eluting with hexanes (100 ml), the column was eluted with ethyl acetate. The ethyl acetate eluent was evaporated to give 3.71 g of a colorless oil; MS m/e 371 (MH+).

후처리

  1. temperatureat reflux for 18 hr
  2. filtrationfiltered through Magnesol
  3. washThe filter pad was eluted with 2×10 ml of ethyl acetate
  4. customthe combined filtrate was evaporated
  5. dissolutionThe residue was dissolved in hexanes
  6. washAfter eluting with hexanes (100 ml)
  7. washthe column was eluted with ethyl acetate
  8. customThe ethyl acetate eluent was evaporated

출처 및 근거

ORD 기록
ord-dc0e98263b6d4278868b76463ebc9e62
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07812014B2

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