Trifluoroacetic acid → 4,6-Di-tert-butyl-5-hydroxypyrimidine-2-carbaldehyde

HRID 1647416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1647416
FC(F)(F)C(O)=O.[CH3:8][C:9]([C:12]1[C:17]([O:18]COCCOC)=[C:16]([C:25]([CH3:28])([CH3:27])[CH3:26])[N:15]=[C:14]([CH:29]=[O:30])[N:13]=1)([CH3:11])[CH3:10].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:11][C:9]([C:12]1[C:17]([OH:18])=[C:16]([C:25]([CH3:28])([CH3:27])[CH3:26])[N:15]=[C:14]([CH:29]=[O:30])[N:13]=1)([CH3:8])[CH3:10]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 199229924,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-2-pyrimidine carboxaldehyde

Produkt 1

HCID 152948964,6-Di-tert-butyl-5-hydroxypyrimidine-2-carbaldehydeAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (1.05 g, 9.2 mmol) is added to a solution of 4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-2-pyrimidine carboxaldehyde (1.0 g, 3.1 mmol) in methylene chloride and the reaction mixture is stirred at room temperature for 5 hours. The reaction mixture is neutralized by the addition of saturated aqueous NaHCO3 and the layers separated. The organic layer is washed with brine (50 mL), dried over MgSO4, and evaporated. Recrystallization of the residue from hexane gives pure 4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxaldehyde(0.24 g, 33% ); mp 187°-189° C.

Aufarbeitung

  1. customthe layers separated
  2. washThe organic layer is washed with brine (50 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customRecrystallization of the residue from hexane

Quellen und Nachweise

ORD-Eintrag
ord-5bc40aa6822c440aa550db382724c568
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05432181

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