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

HRID 978992Notes

Reaction equation

HRID 978992 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 867415245-(3-Acetyl-2,4,6-trimethylphenyl)-2-[1-(ethoxyimino)butyl]-3-(4-toluenesulfonyl)oxy-cyclohex-2-en-1-oneYield 95.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

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-cc4fef3e2230476087e7179769de5c4b
Source dataset
uspto-grants-1987_05
Patent number
US04666510

Reaction notes

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