Clofibrate → Clofibric Acid

HRID 1430616

反応式

HRID 1430616 の反応式
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

参加物

4

反応物 2

HCID 2796ClofibrateHCID 3939Lithium Hydroxide

生成物 1

HCID 2797Clofibric Acid収率 20.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-850b74c115a340d2bf0a5b20f5497a0d
出典データセット
uspto-grants-2015_01
特許番号
US08940900B2

関連ノート

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