p-Toluenesulfonic acid → HCID 54554954, compound

HRID 343752Notes

Reaction equation

HRID 343752 reaction equation
C(OC([CH:8]([C:14]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:18]([O:26][CH2:27][CH3:28])[C:17]=1[CH3:29])=[O:15])[C:9]([CH:11]1[CH2:13][CH2:12]1)=[O:10])=O)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:11]1([C:9](=[O:10])[CH2:8][C:14]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:18]([O:26][CH2:27][CH3:28])[C:17]=2[CH3:29])=[O:15])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 54571808HCID 54571808, compound

Product 1

HCID 54554954HCID 54554954, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of crude 2-tert-butoxycarbonyl-1-cyclopropyl-3-(2-methyl-3-ethoxy-4-methylsulfonylphenyl)-1,3-propanedione (10 g) and 4-toluenesulfonic acid (2 g) in dry toluene (150 mL) was stirred and heated at reflux for 2 hours. The cooled mixture was washed with a saturated sodium bicarbonate solution (50 mL), dried over magnesium sulfate, and concentrated in vacuo to afford 7 g of the crude product as a yellow oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. washThe cooled mixture was washed with a saturated sodium bicarbonate solution (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54d142619a8e4589ad3a9b278c5bdd1f
Source dataset
uspto-grants-1999_01
Patent number
US05863865

Reaction notes

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