Ethanol → (E)-(S)-3-[4-(3-biphenyl-4-yl-but-2-enyloxy)-phenyl]-2-ethoxy-propionic acid

HRID 1270057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1270057
[OH-].[Na+].C([O:5][C:6](=[O:31])[C@@H:7]([O:28][CH2:29][CH3:30])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16]/[CH:17]=[C:18](/[CH3:27])\[C:19]#CC2C=CC=CC=2)=[CH:11][CH:10]=1)C.[CH2:32](O)[CH3:33]>>[C:8]1([C:33]2[CH:32]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=[CH:10][C:19](/[C:18](/[CH3:27])=[CH:17]/[CH2:16][O:15][C:12]2[CH:11]=[CH:10][C:9]([CH2:8][C@H:7]([O:28][CH2:29][CH3:30])[C:6]([OH:5])=[O:31])=[CH:14][CH:13]=2)=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 86583976(Z)-(S)-2-ethoxy-3-[4-(3-methyl-5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-propionic acid ethyl ester

Produkt 1

HCID 10093355(E)-(S)-3-[4-(3-biphenyl-4-yl-but-2-enyloxy)-phenyl]-2-ethoxy-propionic acid

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Sodium hydroxide (1N, 1.25 mL, 1.25 mmol) was added to a solution of (Z)-(S)-2-ethoxy-3-[4-(3-methyl-5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-propionic acid ethyl ester (example 3) (0.246 g, 0.627 mmol) in ethanol (20 mL) and the mixture stirred at 70° C. for 2.5 h. After cooling to room temperature the resulting mixture was partitioned between water (50 mL) and ethyl acetate (50 mL). The aqueous phase was collected, acidified with 1N hydrochloric acid (5 mL) and extracted into ethyl acetate (100 mL). The organic phase was washed with brine, dried (Na2SO4) and evaporated to give (E)-(S)-3-[4-(3-biphenyl-4-yl-but-2-enyloxy)-phenyl]-2-ethoxy-propionic acid as an oil; 0.150 g (66%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature the resulting mixture
  2. customwas partitioned between water (50 mL) and ethyl acetate (50 mL)
  3. customThe aqueous phase was collected
  4. extractionextracted into ethyl acetate (100 mL)
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-be23f29fbd624f5980c202ff69700385
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202213B2

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