4-Toluenesulfonyl chloride → 5-(3-Acetyl-2,4,6-trimethylphenyl)-2-[1-(ethoxyimino)butyl]-3-(4-toluenesulfonyl)oxy-cyclohex-2-en-1-one

HRID 978992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 978992
[Na].[C:2]([C:5]1[C:6]([CH3:29])=[C:7]([CH:13]2[CH2:18][C:17](=[O:19])[C:16]([C:20](=[N:24][O:25][CH2:26][CH3:27])[CH2:21][CH2:22][CH3:23])=[C:15]([OH:28])[CH2:14]2)[C:8]([CH3:12])=[CH:9][C:10]=1[CH3:11])(=[O:4])[CH3:3].[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>CC(C)=O>[C:2]([C:5]1[C:6]([CH3:29])=[C:7]([CH:13]2[CH2:14][C:15](=[O:28])[C:16]([C:20](=[N:24][O:25][CH2:26][CH3:27])[CH2:21][CH2:22][CH3:23])=[C:17]([O:19][S:36]([C:33]3[CH:34]=[CH:35][C:30]([CH3:40])=[CH:31][CH:32]=3)(=[O:38])=[O:37])[CH2:18]2)[C:8]([CH3:12])=[CH:9][C:10]=1[CH3:11])(=[O:4])[CH3:3]

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 5360545SodiumHCID 136058378HCID 136058378, Verbindung

Produkt 1

HCID 867415245-(3-Acetyl-2,4,6-trimethylphenyl)-2-[1-(ethoxyimino)butyl]-3-(4-toluenesulfonyl)oxy-cyclohex-2-en-1-oneAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

The sodium salt of 5-(3-acetyl-2,4,6-trimethylphenyl)-2-[1-(ethoxyimino)butyl]-3-hydroxy-cyclohex-2-en-1-one (0.10 g; 0.26 mmole) was dissolved in acetone and then 4-toluenesulfonyl chloride (0.05 g; 0.26 mmole) was added. The mixture was stirred for 15 minutes and then the solvent was removed by evaporation under reduced pressure using a rotary evaporator. The product was purified by column chromatography over silica gel (eluant dichloromethane) to give 5-(3-acetyl-2,4,6-trimethylphenyl)-2-[1-(ethoxyimino)butyl]-3-(4-toluenesulfonyl)oxy-cyclohex-2-en-1-one (0.13 g; 95.6%) as a yellow oil.

Aufarbeitung

  1. customthe solvent was removed by evaporation under reduced pressure
  2. customa rotary evaporator
  3. customThe product was purified by column chromatography over silica gel (eluant dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-cc4fef3e2230476087e7179769de5c4b
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04666510

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