Butyryl chloride → (+)-2-(4-(3-Butyryloxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidine

HRID 1163

Reaktionsgleichung

Reaktionsgleichung von HRID 1163
[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:32](Cl)(=[O:36])[CH2:33][CH2:34][CH3:35]>N1C=CC=CC=1.C1(C)C=CC=CC=1>[C:32]([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)(=[O:36])[CH2:33][CH2:34][CH3:35]

Komponenten

5

Edukt 2

HCID 8855Butyryl chlorideHCID 54106197(-)-2-(4-(3-Hydroxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidine

Produkt 1

HCID 54507690(+)-2-(4-(3-Butyryloxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidineAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

1.0 g of (-)-2-(4-(3-hydroxy-4,4,4-trifluoro-1-butenyl) phenyl)-5-decyloxypyrimidine was dissolved in 20 ml of pyridine. The solution was added with 0.5 g of butyryl chloride and stirred at 25°-30° C. for 4 hours. The reaction mixture was diluted with 100 ml of toluene and washed with 4N hydrochloric acid, water, a 5% sodium bicarbonate solution and water successively in that order, and then the toluene layer was concentrated under reduced pressure. The residue was purified by subjecting it to silica gel column chromatography using toluene/ethyl acetate as eluent to obtain 1.08 g of (+)-2-(4-(3-butyryloxy-4,4,4-trifluoro-1-butenyl) phenyl)-5-decyloxy-pyrimidine.

Aufarbeitung

  1. washwashed with 4N hydrochloric acid, water
  2. concentrationa 5% sodium bicarbonate solution and water successively in that order, and then the toluene layer was concentrated under reduced pressure
  3. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-a527bf234aeb411088cf0a7588b93b15
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723610

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