Potassium Hydroxide → Rac-cyclopentyloxy-(3,4-dichloro-phenyl)-acetic acid

HRID 397181ノート

反応式

HRID 397181 の反応式
C[O:2][C:3](=[O:19])[CH:4]([O:13][CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1.[OH-].[K+]>C(O)C.O>[CH:14]1([O:13][CH:4]([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=2)[C:3]([OH:19])=[O:2])[CH2:18][CH2:17][CH2:16][CH2:15]1

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 12044173Rac-cyclopentyloxy-(3,4-dichloro-phenyl)-acetic acid methyl ester

生成物 1

HCID 12044174Rac-cyclopentyloxy-(3,4-dichloro-phenyl)-acetic acid収率 88%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
25 °C

実験手順

A solution of rac-cyclopentyloxy-(3,4-dichloro-phenyl)-acetic acid methyl ester (266 mg, 0.877 mmol) in ethanol (10 mL) was treated with a solution of potassium hydroxide (123 mg, 2.19 mmol) in water (1 mL) and the mixture was stirred at 25° C. After 3 h, the reaction was diluted with water (5 mL) and the ethanol was removed in vacuo. The aqueous layer was then acidified to pH 2 with 1 N hydrochloric acid and extracted with dichloromethane (3×15 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 chloroform/methanol plus 1% acetic acid) to afford rac-cyclopentyloxy-(3,4-dichloro-phenyl)-acetic acid (223 mg, 88% yield) as a white solid, mp 87.5-89.9 IC; EI-HRMS m/e calcd for C13H14Cl2O3 (M+) 288.0320, found 288.0332.

後処理

  1. customthe ethanol was removed in vacuo
  2. extractionextracted with dichloromethane (3×15 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 chloroform/methanol plus 1% acetic acid)

出典と根拠

ORDレコード
ord-bbc6b5b50b9644fcb088da858e78e6b6
出典データセット
uspto-grants-2003_08
特許番号
US06608218B2

反応ノート

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