4-Toluenesulfonyl chloride → HCID 73771261, compound

HRID 1382171Notes

Reaction equation

HRID 1382171 reaction equation
[O-]CC.[Na+].[CH2:5]([O:7][N:8]=[C:9]([C:12]1[C:13](=[O:31])[CH2:14][CH:15]([C:19]2[C:24]([CH3:25])=[C:23]([CH3:26])[C:22]([CH3:27])=[C:21]([CH3:28])[C:20]=2[O:29][CH3:30])[CH2:16][C:17]=1[OH:18])[CH2:10][CH3:11])[CH3:6].[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>C(O)C>[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38]([O:31][C:13]2[CH2:14][CH:15]([C:19]3[C:24]([CH3:25])=[C:23]([CH3:26])[C:22]([CH3:27])=[C:21]([CH3:28])[C:20]=3[O:29][CH3:30])[CH2:16][C:17](=[O:18])[C:12]=2[C:9](=[N:8][O:7][CH2:5][CH3:6])[CH2:10][CH3:11])(=[O:40])=[O:39])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 2723922Sodium ethoxideHCID 136127123HCID 136127123, compound

Product 1

HCID 73771261HCID 73771261, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of sodium ethoxide (1.10 mmole) in ethanol (8.2 ml) was added to a solution of 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(2-methoxy-3,4,5,6-tetramethylphenyl)cyclohex-2-en-1-one (0.40 g, 1.10 mmole) in ethanol (50 ml). The mixture was evaporated to dryness and the residue dissolved in acetone (50 ml). 4-Toluenesulfonyl chloride (0.21 g, 1.10 mmole) was added and the mixture was stirred at room temperature for 2 hours, then evaporated to dryness under reduced pressure. The residue was purified by column chromatography over silica gel (eluant dichloromethane) to give 3-(4-toluenesulfonyl)oxy-2-[1-(ethoxyimino)propyl]-5-(2-methoxy-3,4,5,6-tetramethylphenyl)cyclohex-2-en-1-one (0.59 g; 100%) as a yellow oil.

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutionthe residue dissolved in acetone (50 ml)
  3. customevaporated to dryness under reduced pressure
  4. customThe residue was purified by column chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-9819ad1fff684684b24bda3a2f80c145
Source dataset
uspto-grants-1989_02
Patent number
US04806141

Reaction notes

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