Réaction #64054

ord-c2921b43f31b40c995393c8aed70fec6

Équation de réaction

[Na]
sodium
CCCC(=NOCC)C1=C(O)C(c2cc(C)c(C)c(C(C)=O)c2C)CCC1=O
3-acetyl-2,4,5-trimethylphenyl-2-[1-(ethoxyimino)butyl]-3-hydroxy-cyclohex-2-en-1-one
CC(C)=O
acetone
O=C(Cl)c1ccc([N+](=O)[O-])cc1
4-nitrobenzoyl chloride
→
CCCC(=NOCC)C1=C(OC(=O)c2ccc([N+](=O)[O-])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-nitrobenzoyl)oxy-cyclohex-2-en-1-one
Rendement 93.6%

Réactifs

[Na]
sodium
CCCC(=NOCC)C1=C(O)C(c2cc(C)c(C)c(C(C)=O)c2C)CCC1=O
3-acetyl-2,4,5-trimethylphenyl-2-[1-(ethoxyimino)butyl]-3-hydroxy-cyclohex-2-en-1-one
CC(C)=O
acetone
O=C(Cl)c1ccc([N+](=O)[O-])cc1
4-nitrobenzoyl chloride

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

The sodium salt of 5-(3-acetyl-2,4,5-trimethylphenyl-2-[1-(ethoxyimino)butyl]-3-hydroxy-cyclohex-2-en-1-one (0.13 g; 0.33 mmole) was dissolved in acetone and then 4-nitrobenzoyl chloride (0.06 g; 0.33 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-nitrobenzoyl)oxy-cyclohex-2-en-1-one (0.16 g; 93.6%) as a yellow oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04767879uspto-grants-1988_08