Clofibrate → Clofibric Acid

HRID 1430616

반응식

HRID 1430616 반응식
C([O:3][C:4](=[O:16])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])C.[Li+].[OH-]>C1COCC1>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:16])=[O:3])=[CH:14][CH:13]=1

참가 물질

4

반응물 2

HCID 2796ClofibrateHCID 3939Lithium Hydroxide

생성물 1

HCID 2797Clofibric Acid수율 20.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-(4-Chloro-phenoxy)-2-methyl-propionic acid ethyl ester (6 g, 24.79 mmol) in THF (20 ml) was added a solution of LiOH (3 g, 74.38 mmol) in H20 (4 ml). The resulting solution was stirred at room temperature for 12 hours. After evaporation of the solvent, the residue was diluted with ethyl acetate (100 ml); cool to 0° C., acidified with 1N HCl (PH˜3-4). The organic phase were washed with, brine (20 ml) and dried over Na2SO4. After evaporation, the residue was purified by flash chromatography (1:1 hexanes/EtOAc) to give 2-(4-Chloro-phenoxy)-2-methyl-propionic acid (1.1 g, 20%). 1H NMR (400 MHz, CDCl3): δ 1.60 (s, 6H), 6.85 (d, J=8.7 Hz, 2H), 7.22 (d, J=8.7 Hz, 2H). MS (EI) m/z: 215.5 (M+1).

후처리

  1. customAfter evaporation of the solvent
  2. additionthe residue was diluted with ethyl acetate (100 ml)
  3. temperaturecool to 0° C.
  4. washThe organic phase were washed with, brine (20 ml)
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation
  7. customthe residue was purified by flash chromatography (1:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-850b74c115a340d2bf0a5b20f5497a0d
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940900B2

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