Hydrochloric Acid → 2-(Allyloxy)-6-{[(4'-{[(allyloxy)carbonyl]methyl}-3-fluoro-1,1'-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoic acid

HRID 2076605

Reaktionsgleichung

Reaktionsgleichung von HRID 2076605
Cl([O-])=O.[Na+].O.P([O-])(O)(O)=O.[Na+].[CH2:12]([O:15][C:16]1[C:17]([CH:48]=[O:49])=[C:18]([CH:41]=[CH:42][C:43]=1[C:44]([F:47])([F:46])[F:45])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])=[CH:29][CH:28]=2)=[CH:23][C:22]=1[F:40])[CH:13]=[CH2:14].CC(=CC)C.S([O-])([O-])(=[O:57])=S.[Na+].[Na+].Cl>C(O)(C)(C)C.O1CCOCC1>[CH2:12]([O:15][C:16]1[C:43]([C:44]([F:46])([F:47])[F:45])=[CH:42][CH:41]=[C:18]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:28]=[CH:29][C:30]([CH2:33][C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])=[CH:31][CH:32]=3)=[CH:23][C:22]=2[F:40])[C:17]=1[C:48]([OH:57])=[O:49])[CH:13]=[CH2:14]

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 24477Sodium ThiosulfateHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 86617403Allyl (4'-{[3-(allyloxy)-2-formyl-4-(trifluoromethyl)benzyl]oxy}-3'-fluoro-1,1'-biphenyl-4-yl)acetate

Produkt 1

HCID 671189772-(Allyloxy)-6-{[(4'-{[(allyloxy)carbonyl]methyl}-3-fluoro-1,1'-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6386tert-ButanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

After an aqueous solution (1.1 ml) of sodium chlorite (125 mg, 1.38 mmol) and sodium dihydrogenphosphate monohydrate (125 mg, 0.91 mmol) was added dropwise to a solution of allyl (4′-{[3-(allyloxy)-2-formyl-4-(trifluoromethyl)benzyl]oxy}-3′-fluoro-1,1′-biphenyl-4-yl)acetate obtained in Example (12-5) in a mixture of tert-butyl alcohol (2.4 ml), 1,4-dioxane (0.8 ml) and 2-methyl-2-butene (0.8 ml), the mixture was stirred at room temperature for 2 hours. After a 5% aqueous sodium thiosulfate solution was added to the reaction mixture, the mixture was poured into 1N hydrochloric acid and extracted with ethyl acetate (twice). The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a residue. The obtained residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate) to give 2-(allyloxy)-6-{[(4′-{[(allyloxy)carbonyl]methyl}-3-fluoro-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoic acid (135 mg, yield: 100%).

Aufarbeitung

  1. extractionextracted with ethyl acetate (twice)
  2. washThe organic layer was successively washed with water
  3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customto give a residue
  6. customThe obtained residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d502c9860e664dd8b70dd773575336a1
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923573B2

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