Reaktion #64055

ord-6b9dbaa68fa94df3a31a516d4d7b2605

Reaktionsgleichung

[Na]
sodium
CCCC(=NOCC)C1=C(O)CC(c2c(C)cc(C)c(C(C)=O)c2C)CC1=O
5-(3-acetyl-2,4,6-trimethylphenyl)-2-[1-(ethoxyimino)butyl]-3-hydroxy-cyclohex-2-en-1-one
Cc1ccc(S(=O)(=O)Cl)cc1
4-toluenesulfonyl chloride
→
CCCC(=NOCC)C1=C(OS(=O)(=O)c2ccc(C)cc2)CC(c2c(C)cc(C)c(C(C)=O)c2C)CC1=O
5-(3-acetyl-2,4,6-trimethylphenyl)-2-[1-(ethoxyimino)butyl]-3-(4-toluenesulfonyl)oxy-cyclohex-2-en-1-one
Ausbeute 95.6%

Edukte

[Na]
sodium
CCCC(=NOCC)C1=C(O)CC(c2c(C)cc(C)c(C(C)=O)c2C)CC1=O
5-(3-acetyl-2,4,6-trimethylphenyl)-2-[1-(ethoxyimino)butyl]-3-hydroxy-cyclohex-2-en-1-one
Cc1ccc(S(=O)(=O)Cl)cc1
4-toluenesulfonyl chloride

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04767879uspto-grants-1988_08