(4-{3-[3-Bromo-5-(4-trifluoromethyl-phenylethynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester → (4-{3-[3-Bromo-5-(4-trifluoromethyl-phenylethynyl)-phenyl]-prop-2-ynyloxy}-2-methylphenoxy)-acetic acid

HRID 548571Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 548571
C[O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]#[C:15][C:16]2[CH:21]=[C:20]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[CH:19]=[C:18]([Br:34])[CH:17]=2)=[CH:8][C:7]=1[CH3:35]>C(O)C.[OH-].[Na+]>[Br:34][C:18]1[CH:17]=[C:16]([C:15]#[C:14][CH2:13][O:12][C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:36])=[O:2])=[C:7]([CH3:35])[CH:8]=2)[CH:21]=[C:20]([C:22]#[C:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:26][CH:25]=2)[CH:19]=1

Komponenten

4

Edukt 1

HCID 67159034(4-{3-[3-Bromo-5-(4-trifluoromethyl-phenylethynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester

Produkt 1

HCID 24752743(4-{3-[3-Bromo-5-(4-trifluoromethyl-phenylethynyl)-phenyl]-prop-2-ynyloxy}-2-methylphenoxy)-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of (4-{3-[3-bromo-5-(4-trifluoromethyl-phenylethynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester (94 mg, 0.169 mmol) in ethanol (5 ml) and 1N NaOH (0.5 ml) was stirred at 75° C. for 30 min. The reaction mixture was evaporated and the residue dissolved in water (2 ml). Aqueous 1N HCl (0.6 ml) was added and the mixture was extracted with methylene chloride (3×15 ml). The combined organic phases were dried and evaporated to give the title compound in 79 mg (86%) yield.

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue dissolved in water (2 ml)
  3. additionAqueous 1N HCl (0.6 ml) was added
  4. extractionthe mixture was extracted with methylene chloride (3×15 ml)
  5. customThe combined organic phases were dried
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c7c46ac3bd344538b62c47b77f5a88c4
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943612B2

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