Butyryl chloride → (+)-2-(4-(3-Butyryloxy-1-butenyl)phenyl)-5-decyloxy-pyrimidine

HRID 1165

Reaktionsgleichung

Reaktionsgleichung von HRID 1165
[OH:1][CH:2]([CH3:28])[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:29](Cl)(=[O:33])[CH2:30][CH2:31][CH3:32]>N1C=CC=CC=1.C1(C)C=CC=CC=1>[C:29]([O:1][CH:2]([CH3:28])[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:33])[CH2:30][CH2:31][CH3:32]

Komponenten

5

Edukt 2

HCID 8855Butyryl chlorideHCID 54343164(-)-2-(4-(3-Hydroxy-1-butenyl)phenyl)-5-decyloxypyrimidine

Produkt 1

HCID 54572593(+)-2-(4-(3-Butyryloxy-1-butenyl)phenyl)-5-decyloxy-pyrimidineAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

1.0 g of (-)-2-(4-(3-hydroxy-1-butenyl)phenyl)-5-decyloxypyrimidine was dissolved in 20 ml of pyridine, 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. The toluene layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography using toluene/ethyl acetate as eluent to obtain 1.05 g of (+)-2-(4-(3-butyryloxy-1-butenyl)phenyl)-5-decyloxy-pyrimidine.

Aufarbeitung

  1. washwashed with 4N hydrochloric acid, water
  2. concentrationThe toluene layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9b515fcf22a54464836bc78f7d1d5c2e
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723610

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