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Sodium Hydroxide → (E)-(4'-{1-ethyl-1-[4-(3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-biphenyl-4-yl)-acetic Acid

HRID 546911
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 546911
[OH-].[Na+].C[O:4][C:5](=[O:39])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH2:37][CH3:38])([C:22]3[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]([CH2:34][CH3:35])([OH:33])[CH2:31][CH3:32])=[C:24]([CH3:36])[CH:23]=3)[CH2:20][CH3:21])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[Cl-].[NH4+]>CO.O1CCCC1>[CH2:20]([C:19]([C:16]1[CH:15]=[CH:14][C:13]([C:10]2[CH:9]=[CH:8][C:7]([CH2:6][C:5]([OH:39])=[O:4])=[CH:12][CH:11]=2)=[CH:18][CH:17]=1)([C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]([CH2:31][CH3:32])([OH:33])[CH2:34][CH3:35])=[C:24]([CH3:36])[CH:23]=1)[CH2:37][CH3:38])[CH3:21]
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Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 57709038(E)-(4'-{1-ethyl-1-[4-(3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-biphenyl-4-yl)acetic acid methyl ester

Produkt 1

HCID 57708979(E)-(4'-{1-ethyl-1-[4-(3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-biphenyl-4-yl)-acetic AcidAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815
MeOH tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A 1 N sodium hydroxide aqueous solution (0.293 mL, 0.293 mmol) was added to a solution of (E)-(4′-{1-ethyl-1-[4-(3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-biphenyl-4-yl)acetic acid methyl ester (Example 59-(1); 48.7 mg, 0.098 mmol) in methanol-tetrahydrofuran (1:1, 4 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=1:1) to give the target compound as a colorless oil (38.8 mg, 82%).

Aufarbeitung

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-bf6a079081f3439e8b4f14e478a44eab
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07935688B2

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