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Sodium Hydroxide → (E)-4-cyclopentyl-2-[4-(methanesulfonyl)-3-(trifluoromethyl)-phenyl)-but-2-enoic acid

HRID 276232
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HRID 276232 반응식
C[O:2][C:3](=[O:26])/[C:4](/[C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[C:14]([C:22]([F:25])([F:24])[F:23])[CH:13]=1)=[CH:5]/[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-].[Na+]>C(O)C>[CH:7]1([CH2:6]/[CH:5]=[C:4](\[C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[C:14]([C:22]([F:25])([F:23])[F:24])[CH:13]=2)/[C:3]([OH:26])=[O:2])[CH2:11][CH2:10][CH2:9][CH2:8]1
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참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 67482895(E)-4-cyclopentyl-2-(4-(methanesulfonyl)-3-(trifluoromethyl)-phenyl)-but-2-enoic acid methyl ester

생성물 1

HCID 67483112(E)-4-cyclopentyl-2-[4-(methanesulfonyl)-3-(trifluoromethyl)-phenyl)-but-2-enoic acid수율 92.4%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
40 °C

실험 절차

A solution of (E)-4-cyclopentyl-2-[4-(methanesulfonyl)-3-(trifluoromethyl)-phenyl)-but-2-enoic acid methyl ester (0.82 g, 2.1 mmol) in ethanol (10 mL) was treated with a 1N aqueous sodium hydroxide solution (5 mL). The solution was heated at 40° C. for 15 h, at which time, thin layer chromatography analysis of the mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo to remove ethanol, and the residue was diluted with water (30 mL) and extracted with diethyl ether (1×50 mL) to remove any neutral impurities. The aqueous layer was acidified with a 1N aqueous hydrochloric acid solution. The resulting acid was extracted into ethyl acetate (2×50 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×80 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford (E)-4-cyclopentyl-2-[4-(methanesulfonyl)-3-(trifluoromethyl)-phenyl)-but-2-enoic acid (0.73 g, 92%) as a gummy solid: EI-HRMS m/e calcd for C17H19F3O4S (M+) 376.0243, found 376.0261.

후처리

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customto remove ethanol
  3. additionthe residue was diluted with water (30 mL)
  4. extractionextracted with diethyl ether (1×50 mL)
  5. customto remove any neutral impurities
  6. extractionThe resulting acid was extracted into ethyl acetate (2×50 mL)
  7. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×80 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-aa5e79e43c4e42eeade20d38d1d3c857
출처 데이터셋
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06353111B1

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