p-Toluenesulfonic acid → HCID 18989191, compound

HRID 2395551Notes

Reaction equation

HRID 2395551 reaction equation
[CH:1]1([C:4](=[O:28])[CH:5](C(OC(C)(C)C)=O)[C:6]([C:8]2[C:16]3[O:15][C:14]([F:18])([F:17])[O:13][C:12]=3[C:11]([S:19][CH3:20])=[CH:10][CH:9]=2)=[O:7])[CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:1]1([C:4](=[O:28])[CH2:5][C:6]([C:8]2[C:16]3[O:15][C:14]([F:18])([F:17])[O:13][C:12]=3[C:11]([S:19][CH3:20])=[CH:10][CH:9]=2)=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 18989178HCID 18989178, compound

Product 1

HCID 18989191HCID 18989191, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-(3-cyclopropyl-2-t-butyloxycarbonyl-1,3-dioxoprop-1-yl)-2,2-difluoro-7-methylsulphenyl-1,3-benzodioxole (10.3 g) and para-toluenesulphonic acid (0.5 g) was heated under reflux with toluene for 3 hours. After cooling, the solvent was evaporated in vacuo, and ethyl acetate added. The solution was washed with water, dried over anhydrous magnesium sulphate and evaporated. The residue was purified by column chromatography, eluting with ethyl acetate/cyclohexane to yield 4-(3-cyclopropyl-1,3-dioxoprop-1-yl)-2,2-difluoro-7-methylsulphenyl-1,3-benzodioxole (6.61 g) m.p. 117.5°-118.5° C.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated in vacuo, and ethyl acetate
  3. additionadded
  4. washThe solution was washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washeluting with ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-77eb080df34740a0a639bb4147170670
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

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