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Potassium Hydroxide → 2-[trans-3-(3-Carboxy-3,3-dimethylpropyloxy)styryl]-4-isopropylthiazole

HRID 1199712
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HRID 1199712 반응식
[CH3:1][C:2]([CH3:27])([C:22]([O:24]CC)=[O:23])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:19]=[CH:20][CH:21]=1)/[CH:9]=[CH:10]/[C:11]1[S:12][CH:13]=[C:14]([CH:16]([CH3:18])[CH3:17])[N:15]=1.[OH-].[K+]>C(O)C.CO.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>[C:22]([C:2]([CH3:27])([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:19]=[CH:20][CH:21]=1)/[CH:9]=[CH:10]/[C:11]1[S:12][CH:13]=[C:14]([CH:16]([CH3:17])[CH3:18])[N:15]=1)([OH:24])=[O:23]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 157184372-[trans-3-(3,3-Dimethyl-3-ethoxycarbonylpropyloxy)styryl]-4-isopropylthiazole

생성물 1

HCID 157184452-[trans-3-(3-Carboxy-3,3-dimethylpropyloxy)styryl]-4-isopropylthiazole수율 66.3%

시약·촉매·용매 2

HCID 19865511Benzyltrimethylammonium hydroxide methanol촉매HCID 702Ethanol
용매
2회

실험 절차

To a solution of 200 mg of 2-[trans-3-(3,3-dimethyl-3-ethoxycarbonylpropyloxy)styryl]-4-isopropylthiazole dissolved in 5 ml of ethanol were added 2 ml of 10% aqueous potassium hydroxide solution and three drops of 40% benzyltrimethylammonium hydroxide methanol solution, and the mixture was refluxed for 1 hour to effect hydrolysis of the ester. After completion of the reaction, ethanol was evaporated under reduced pressure and the residue was adjusted to pH 1-2 with addition of 10% hydrochloric acid and then extracted with ethyl ether. After drying of anhydrous magnesium sulfate, the solvent was evaporated and the solid formed was recrystallized from methanol to give 123 mg (yield 66%) of the title compound.

후처리

  1. temperaturethe mixture was refluxed for 1 hour
  2. customwas evaporated under reduced pressure
  3. additionthe residue was adjusted to pH 1-2 with addition of 10% hydrochloric acid
  4. extractionextracted with ethyl ether
  5. dry with materialAfter drying of anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customthe solid formed
  8. customwas recrystallized from methanol

출처 및 근거

ORD 기록
ord-b01298d2f61f4bfc8091e8fc4020f061
출처 데이터셋
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04902700

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