p-Toluenesulfonic acid → HCID 9884605, compound

HRID 568068Notes

Reaction equation

HRID 568068 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH:31]2[CH2:35][CH2:34][O:33][C:32]2=[O:36])(O)[C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[F:12][C:13]1[CH:18]=[CH:17][C:16](/[C:19](=[C:31]2\[C:32](=[O:36])[O:33][CH2:34][CH2:35]\2)/[C:20]2[CH:21]=[CH:22][C:23]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:24][CH:25]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15383994HCID 15383994, compound

Product 1

HCID 9884605HCID 9884605, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A few mg of toluene-4-sulphonic acid are added to a solution of 7 g of 3-[1-(4-fluorophenyl)-1-hydroxy-1-(4-methanesulphonylphenyl)methyl]dihydrofuran-2-one, prepared in Example 3, in 100 ml of toluene and the mixture is refluxed for 10 hours in a Dean-Stark apparatus. The solvent is then evaporated off to dryness under vacuum and the residue is chromatographed using a 9/1 dichloromethanel/acetone mixture as the eluent to give an oil, which is chromatographed using t-butyl methyl ether as the eluent to give 2.9 g of (E)-3-[1-(4-fluorophenyl)-1-(4-methanesulphonylphenyl)methylidene]dihydrofuran-2-one (second product eluted) in the form of crystals melting at 187-9° C. 1.5 g of (Z)-3-[1-(4-fluorophenyl)-1-(4-methanesulphonylphenyl)methylidene]dihydrofuran-2-one (first product eluted) are recovered in the form of crystals melting at 157-158° C.

Workup

  1. temperaturethe mixture is refluxed for 10 hours in a Dean-Stark apparatus
  2. customThe solvent is then evaporated off to dryness under vacuum
  3. customthe residue is chromatographed
  4. customto give an oil, which
  5. customis chromatographed

Sources & evidence

ORD record
ord-98a33111491e4604bb0793dbe2d30b0b
Source dataset
uspto-grants-2001_01
Patent number
US06180651B2

Reaction notes

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