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Water → HCID 67119321, Verbindung

HRID 2076694
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2076694
[CH2:1]([O:4][C:5]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[C:14]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][C:33]([CH2:36][C:37]([O:39][CH2:40][CH:41]=[CH2:42])=[O:38])=[C:32]([F:43])[CH:31]=3)=[CH:26][CH:25]=2)[C:6]=1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:2]=[CH2:3].C(O[CH:49](OC(C)(C)C)[N:50]([CH3:52])[CH3:51])(C)(C)C.O>C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]1[C:17]([C:18]([F:20])([F:21])[F:19])=[CH:16][CH:15]=[C:14]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([C:37]([O:39][CH2:40][CH:41]=[CH2:42])=[O:38])=[CH:49][N:50]([CH3:52])[CH3:51])=[C:32]([F:43])[CH:31]=3)=[CH:26][CH:25]=2)[C:6]=1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:2]=[CH2:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 67119033HCID 67119033, Verbindung

Produkt 1

HCID 67119321HCID 67119321, VerbindungAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

tert-Butyl 2-(allyloxy)-6-{[(4′-{[(allyloxy)carbonyl]methyl}-3′-fluoro-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoate (200 mg, 0.33 mmol) obtained in Example (11-6) was dissolved in toluene (3 ml) and N,N-dimethylformamide di-tert-butyl acetal (0.4 ml, 1.7 mmol) was added thereto, and the mixture was heated under reflux for 3 hours. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate (three times), the organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=10/1-1/1) to give tert-butyl 2-(allyloxy)-6-{[(4′-{1-[(allyloxy)carbonyl]-2-(dimethylamino)vinyl}-3′-fluoro-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoate (141 mg, yield: 65%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionthe mixture was extracted with ethyl acetate (three times)
  4. washthe organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe residue obtained
  7. customby removing the solvent under reduced pressure
  8. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=10/1-1/1)

Quellen und Nachweise

ORD-Eintrag
ord-9eee123ae2c547159096bec5d453c56f
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07923573B2

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