Water → HCID 18953326, compound

HRID 1491573Notes

Reaction equation

HRID 1491573 reaction equation
[CH:1]1([C:4]([CH:6]([C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]=2[S:29]([CH3:32])(=[O:31])=[O:30])=[O:15])C(OC(C)(C)C)=O)=[O:5])[CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH:1]1([C:4](=[O:5])[CH2:6][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]=2[S:29]([CH3:32])(=[O:31])=[O:30])=[O:15])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 18953296HCID 18953296, compound

Product 1

HCID 18953326HCID 18953326, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of t-butyl 2-cyclopropylcarbonyl-3-(2-methylsulphonyl-3-phenylsulphenylphenyl)-3-oxopropionoate (8.5 g) and para-toluene sulphonic acid (0.25 g) in toluene was heated at reflux for six hours. Water and ethyl acetate were then added and the organic phase was dried over anhydrous sodium sulphate, filtered and evaporated. The residue was crystallised from ether to give 1-cyclopropyl-3-(2-methylsulphonyl-3-phenylsulphenylphenyl)propan-1,3-dione (6.2 g) as a beige powder,

Workup

  1. temperaturewas heated
  2. temperatureat reflux for six hours
  3. dry with materialthe organic phase was dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallised from ether

Sources & evidence

ORD record
ord-22e89ad7531d44f8850227a8ce0ce7a5
Source dataset
uspto-grants-1994_12
Patent number
US05371064

Reaction notes

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