Acetone → HCID 86741522, compound

HRID 35776Notes

Reaction equation

HRID 35776 reaction equation
[Na].C(C1C(C)=C([CH:13]2[CH2:18][CH2:17][C:16](=[O:19])[C:15]([C:20](=[N:24][O:25][CH2:26][CH3:27])[CH2:21][CH2:22][CH3:23])=[C:14]2[OH:28])C=C(C)C=1C)(=O)C.[N+:30]([C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1)([O-:32])=[O:31].[CH3:42][C:43]([CH3:45])=[O:44]>>[C:43]([C:45]1[C:13]([CH3:18])=[C:14]([CH:18]2[CH2:17][C:16](=[O:19])[C:15]([C:20](=[N:24][O:25][CH2:26][CH3:27])[CH2:21][CH2:22][CH3:23])=[C:14]([O:28][C:37](=[O:38])[C:36]3[CH:40]=[CH:41][C:33]([N+:30]([O-:32])=[O:31])=[CH:34][CH:35]=3)[CH2:13]2)[C:15]([CH3:16])=[CH:20][C:21]=1[CH3:22])(=[O:44])[CH3:42]

Participants

5

Reactant 4

HCID 180AcetoneHCID 85024-Nitrobenzoyl chlorideHCID 5360545SodiumHCID 136393662HCID 136393662, compound

Product 1

HCID 86741522HCID 86741522, compoundYield 93.6%

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-c2921b43f31b40c995393c8aed70fec6
Source dataset
uspto-grants-1988_08
Patent number
US04767879

Reaction notes

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