(-)-2-(4-(3-Hydroxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidine → (-)-2-(4-(3-Butoxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidine

HRID 1162

Reaktionsgleichung

Reaktionsgleichung von HRID 1162
[OH:1][CH:2]([C:28]([F:31])([F:30])[F:29])[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:13][N:12]=2)=[CH:7][CH:6]=1>C(I)CCC.[Ag]=O>[CH2:28]([O:1][CH:2]([C:28]([F:30])([F:31])[F:29])[CH:3]=[CH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:13][N:12]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 1

HCID 54106197(-)-2-(4-(3-Hydroxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidine

Produkt 1

HCID 54256226(-)-2-(4-(3-Butoxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidineAusbeute 173,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 92152Silver(II) oxideKatalysatorHCID 10962Butyl iodideLösungsmittel

Versuchsvorschrift

1.0 g of (-)-2-(4-(3-hydroxy-4,4,4-trifluoro-1-butenyl) phenyl)-5-decyloxypyrimidine was dissolved in 5 ml of butyl iodide. The solution was added with 3 g of silver oxide and stirred at 25°-30° C. for 4 days. The reaction mixture was cleared of silver oxide by filtration and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography using toluene/ethyl acetate as eluent to obtain 0.98 g of (-)-2-(4-(3-butoxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidine.

Aufarbeitung

  1. filtrationThe reaction mixture was cleared of silver oxide by filtration
  2. concentrationconcentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-aa775880ee5b480896f2619381c4dc7e
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723610

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