2-Decanol → HCID 21804866, Verbindung

HRID 342510

Reaktionsgleichung

Reaktionsgleichung von HRID 342510
[CH3:1][CH:2]([OH:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H-].[Na+].[H][H].Cl[C:17]1[C:22]([O:23][CH3:24])=[C:21]([O:25][CH2:26][CH3:27])[N:20]=[CH:19][N:18]=1.[Cl-].[NH4+]>CN(C)C=O>[CH3:1][CH:2]([O:11][C:17]1[C:22]([O:23][CH3:24])=[C:21]([O:25][CH2:26][CH3:27])[N:20]=[CH:19][N:18]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Komponenten

7

Edukt 5

HCID 142542-DecanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 543436974-Chloro-5-methoxy-6-ethoxypyrimidineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 21804866HCID 21804866, VerbindungAusbeute 28,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2.7 g (17.0 mmol) of 2-decanol were added dropwise at 50° C. to a suspension of 650 mg (21.6 mmol) of sodium hydride (80% suspension in oil) in 60 ml of dry dimethylformamide, and the mixture was stirred until the evolution of hydrogen had ceased. The mixture was cooled to room temperature and 3.0 g (15.9 mmol) of 4-chloro-5-methoxy-6-ethoxypyrimidine (preparation analogously to Example C) were added in portions. After 30 minutes, the reaction temperature was increased to 50° C., and stirring was continued for 12 hours. The reaction mixture was poured into saturated ammonium chloride solution and subsequently extracted with diethyl ether. The combined organic phase was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel using n-heptane/ethyl acetate (4:1). 1.4 g (28% of theory) of 4-(2-decyloxy)-5-methoxy-6-ethoxypyrimidine were obtained in the form of a yellow oil.

Aufarbeitung

  1. additionwere added in portions
  2. temperaturethe reaction temperature was increased to 50° C.
  3. waitwas continued for 12 hours
  4. extractionsubsequently extracted with diethyl ether
  5. washThe combined organic phase was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-16683827a01c4b7589f6a98a15e89254
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859020

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