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Citric Acid → HCID 86607736, Verbindung

HRID 1622114
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1622114
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][C:22]=1[O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])[CH2:11][NH:12][C:13]([NH:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[CH3:30][O:31][CH2:32][CH2:33][O:34][CH2:35][O:36][C:37]1[C:44](B2OC(C)(C)C(C)(C)O2)=[CH:43][CH:42]=[CH:41][C:38]=1[CH:39]=[O:40].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[C:16]([NH:15][C:13]([NH:12][CH2:11][C:10]1[CH:9]=[C:8]([C:44]2[CH:43]=[CH:42][CH:41]=[C:38]([CH:39]=[O:40])[C:37]=2[O:36][CH2:35][O:34][CH2:33][CH2:32][O:31][CH3:30])[C:22]([O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:21][CH:20]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 66986052HCID 66986052, VerbindungHCID 86607704HCID 86607704, Verbindung

Produkt 1

HCID 86607736HCID 86607736, VerbindungAusbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 2 M solution of potassium carbonate (2.1 mL) was added to a magnetically stirred mixture of 1-[3-bromo-4-(2-methoxyethoxymethoxy)benzyl]-3-tert-butylurea (1.4 g, 4.1 mmol), prepared as in Reference 11, and 2-(2-methoxyethoxymethoxy)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (42 mL, 0.1 mM in toluene, 4.2 mmol), prepared as in Reference 15. The mixture was flushed with nitrogen and then tetrakis(triphenylphosphine)palladium(0) (118 mg, 0.1025 mmol) was added. The mixture was refluxed for 7 hours, cooled and then poured into a mixture of ethyl acetate and 5% citric acid. The organic phase was separated and the aqueous phase was extracted twice more with ethyl acetate. The combined organic phase was dried and concentrated by evaporation. Product was purified from the residue by chromatography on silica gel utilizing 100% ethyl acetate to give 1-tert-butyl-3-[3′-formyl-6,2′-bis-(2-methoxyethoxymethoxy)-biphenyl-3-ylmethyl]-urea (1.2 g).

Aufarbeitung

  1. customThe mixture was flushed with nitrogen
  2. temperatureThe mixture was refluxed for 7 hours
  3. temperaturecooled
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted twice more with ethyl acetate
  6. customThe combined organic phase was dried
  7. concentrationconcentrated by evaporation
  8. customProduct was purified from the residue by chromatography on silica gel utilizing 100% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3716b1e49a814945b5e811ee6f781cef
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08778625B2

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