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

HRID 1019196노트

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HRID 1019196 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

반응 조건

온도
25 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-93891712aba34e4eb69ca1f4de7b238d
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06486184B2

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