Boron tribromide → Allyl 3-{1-[4-(allyloxycarbonyl)-4-methylcyclohexyl]methoxy}-4-hydroxycinnamate

HRID 2225503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2225503
B(Br)(Br)Br.[CH2:5]([O:8][C:9]([C:11]1([CH3:35])[CH2:16][CH2:15][CH:14]([CH2:17][O:18][C:19]2[CH:20]=[C:21]([CH:30]=[CH:31][C:32]=2[O:33]C)[CH:22]=[CH:23][C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25])[CH2:13][CH2:12]1)=[O:10])[CH:6]=[CH2:7].[Cl-].[NH4+]>C(Cl)Cl>[CH2:5]([O:8][C:9]([C:11]1([CH3:35])[CH2:12][CH2:13][CH:14]([CH2:17][O:18][C:19]2[CH:20]=[C:21]([CH:30]=[CH:31][C:32]=2[OH:33])[CH:22]=[CH:23][C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25])[CH2:15][CH2:16]1)=[O:10])[CH:6]=[CH2:7]

Komponenten

5

Edukt 3

HCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 53660565Allyl 3-[1-(4-allyloxycarbonyl-4-methylcyclohexyl)methoxy]-4-methoxycinnamate

Produkt 1

HCID 54284301Allyl 3-{1-[4-(allyloxycarbonyl)-4-methylcyclohexyl]methoxy}-4-hydroxycinnamateAusbeute 38,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

At -78° C., 0.3 ml of boron tribromide was added to a solution of 0.7 g of allyl 3-[1-(4-allyloxycarbonyl-4-methylcyclohexyl)methoxy]-4-methoxycinnamate (Example 47) in 10 ml of methylene chloride. The solution was reacted for 20 minutes in this state. After reaction, 20 ml of an aqueous ammonium chloride solution was added to the reaction solution. The solution was extracted three times with 30 ml of ethyl acetate. The oily substance obtained was washed three times with an aqueous sodium chloride solution and was dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo, yielding 0.26 g of allyl 3-{1-[4-(allyloxycarbonyl)-4-methylcyclohexyl]methoxy}-4-hydroxycinnamate (a compound of the present invention) as a pale yellow oil, which had the following physiochemical properties:

Aufarbeitung

  1. customThe solution was reacted for 20 minutes in this state
  2. additionwas added to the reaction solution
  3. extractionThe solution was extracted three times with 30 ml of ethyl acetate
  4. customThe oily substance obtained
  5. washwas washed three times with an aqueous sodium chloride solution
  6. dry with materialwas dried over magnesium sulfate
  7. customThereafter, the solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-33153a5c13c343b7951a29e5f4c4c222
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05344845

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