Lawesson's reagent → HCID 178460591, compound

HRID 1685808Notes

Reaction equation

HRID 1685808 reaction equation
[O:1]=[C:2]1[CH2:6][S:5][CH2:4][CH:3]1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15](O)=[O:16])=[CH:10][CH:9]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>C1(C)C=CC=CC=1>[O:1]=[C:2]1[CH2:6][S:5][CH2:4][CH:3]1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:16])=[S:28])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 24782883HCID 24782883, compound

Product 1

HCID 178460591HCID 178460591, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-[4-(4-Oxothiolan-3-ylmethyl)phenyl]propionic acid (300 mg) obtained in Example 8 was dissolved in toluene (3.0 ml), and to the solution was added the Lawesson's reagent (729 mg), and then the reaction mixture was refluxed by heating for 4 hours. After completion of the reaction, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (166 mg, 52.4%).

Workup

  1. temperaturethe reaction mixture was refluxed
  2. temperatureby heating for 4 hours
  3. customAfter completion of the reaction
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-5ee4d634683d4eb78fff26b2775f2fe2
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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