p-Toluenesulfonic acid → Ethyl 2-[4-(2-oxothiolan-3-ylidenemethyl)phenyl]propionate

HRID 1685815Notes

Reaction equation

HRID 1685815 reaction equation
O[CH:2]([CH:16]1[CH2:20][CH2:19][S:18][C:17]1=[O:21])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:21]=[C:17]1[C:16](=[CH:2][C:3]2[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=2)[CH2:20][CH2:19][S:18]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59202209Ethyl 2-{4-[hydroxy(2-oxothiolan-3-yl)methyl]phenyl}propionate

Product 1

HCID 67265778Ethyl 2-[4-(2-oxothiolan-3-ylidenemethyl)phenyl]propionateYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 2-{4-[hydroxy(2-oxothiolan-3-yl)methyl]phenyl}propionate (300 mg) obtained in Example 32 was dissolved in toluene (3.0 ml), and to the solution was added p-toluenesulfonic acid (200 mg), and stirred for 1 hour under reflux by heating. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give the title compound (251 mg, 89%).

Workup

  1. temperatureunder reflux
  2. temperatureby heating
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-f4f4db6946e140ef9c6ba501ced214bd
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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