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

HRID 1019196ノート

反応式

HRID 1019196 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° C.; 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-93891712aba34e4eb69ca1f4de7b238d
出典データセット
uspto-grants-2002_11
特許番号
US06486184B2

反応ノート

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