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Methyl (1,8-diethyl-4-oxo-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate → 4-Oxo Etodolac

HRID 1955719
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반응식

HRID 1955719 반응식
C[O:2][C:3](=[O:23])[CH2:4][C:5]1([CH2:21][CH3:22])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8](=[O:20])[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19]>CO.O>[CH2:21]([C:5]1([CH2:4][C:3]([OH:23])=[O:2])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8](=[O:20])[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19])[CH3:22]
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참가 물질

3

반응물 1

HCID 11120627Methyl (1,8-diethyl-4-oxo-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate

생성물 1

HCID 112665954-Oxo Etodolac수율 93.6%

시약·촉매·용매 1

HCID 22242641Methanol--water (1/1)용매

실험 절차

A solution of the product produced in step B (1.25 g, 3.9 mmol), K2 CO3 (3.5 g, 25.3 mmol) and 60 ml MeOH/H2O 1:1 was refluxed for 3 h. The methanol was evaporated, and the aqueous residue acidified to pH 1 using 6N HCl. The aqueous phase was extracted with EtOAc. The organic phase was washed with water, dried (MgSO4), and evaporated to produce a crude glass which was recrystallized from EtOAc-hexane to afford 1.1 g of the title compound as a solid, m. p. 198°-201° C.

후처리

  1. custom
The methanol was evaporated
  • extractionThe aqueous phase was extracted with EtOAc
  • washThe organic phase was washed with water
  • dry with materialdried (MgSO4)
  • customevaporated
  • customto produce a crude glass which
  • customwas recrystallized from EtOAc-hexane
  • 출처 및 근거

    ORD 기록
    ord-c00192f7b2524ef4881fdf06b4db48ed
    출처 데이터셋
    uspto-grants-1998_07
    DOI
    10.6084/m9.figshare.5104873.v1
    특허 번호
    US05776967

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