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Sodium Bicarbonate → 4-Hydroxy-4-(1-(4-chlorophenyl)-5-(p-tolyl)-1H-pyrazol-3-yl)-cyclohexan-1-one

HRID 1802543
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HRID 1802543 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)=[CH:11][C:10]([C:20]3([OH:30])[CH2:29][CH2:28][C:23]4(OCC[O:24]4)[CH2:22][CH2:21]3)=[N:9]2)=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+]>O1CCCC1.Cl>[OH:30][C:20]1([C:10]2[CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)[N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[N:9]=2)[CH2:21][CH2:22][C:23](=[O:24])[CH2:28][CH2:29]1
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참가 물질

5

반응물 2

HCID 516892Sodium BicarbonateHCID 583994018-(1-(4-Chlorophenyl)-5-(p-tolyl)-1H-pyrazol-3-yl)-1,4-dioxaspiro[4.5]decan-8-ol

생성물 1

HCID 461939634-Hydroxy-4-(1-(4-chlorophenyl)-5-(p-tolyl)-1H-pyrazol-3-yl)-cyclohexan-1-one수율 61.6%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 8-(1-(4-chlorophenyl)-5-p-tolyl-1H-pyrazol-3-yl)-1,4-dioxaspiro[4.5]decan-8-ol (Reference Example 34) (931 mg, 2.19 mmol) in tetrahydrofuran (5.5 mL), 6 M hydrochloric acid (11 mL) was added, and the obtained solution was stirred at room temperature for 15 hours. The reaction solution was basified by pouring it into saturated aqueous sodium hydrogen carbonate solution, and the resulting solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate) to obtain the title compound (513 mg, 1.35 mmol, 61%) as a white solid.

후처리

  1. extractionthe resulting solution was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-1942a0c47bd0475ba888a4cb1d68a5e4
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08349874B2

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