Hydrochloric Acid → 2-Methyl-4-[3-(3-methylbenzothiophen-2-yl)propionyl]phenoxyacetic acid

HRID 241361노트

반응식

HRID 241361 반응식
[CH3:1][C:2]1[CH:14]=[C:13]([C:15](=[O:28])[CH2:16][CH2:17][C:18]2[S:19][C:20]3[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=3[C:22]=2[CH3:23])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8]CC)=[O:7].O.O.[OH-].[Li+].Cl>C(O)C>[CH3:1][C:2]1[CH:14]=[C:13]([C:15](=[O:28])[CH2:16][CH2:17][C:18]2[S:19][C:20]3[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=3[C:22]=2[CH3:23])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66884017Ethyl 2-methyl-4-[3-(3-methylbenzothiophen-2-yl)propionyl]phenoxyacetate

생성물 1

HCID 444664652-Methyl-4-[3-(3-methylbenzothiophen-2-yl)propionyl]phenoxyacetic acid수율 59%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of ethyl 2-methyl-4-[3-(3-methylbenzothiophen-2-yl)propionyl]phenoxyacetate in ethanol (2 mL)/water (1 mL) was added lithium hydroxide monohydrate (70 mg, 1.7 mmol). The mixture was heated under reflux for 1 hour, cooled at room temperature. After addition of ice, the resultant mixture was acidified with 1M hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was recrystallized from ethyl acetate/hexane to give the titled compound as a pale yellow crystal (120 mg, 59%).

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. additionAfter addition of ice
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was recrystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-68ce6f8b703842e2abe2215af376ec9a
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648208B2

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