Lawesson's reagent → HCID 12477826, compound

HRID 1186697Notes

Reaction equation

HRID 1186697 reaction equation
[C:1]([CH:9]([CH2:15][C:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1>C1(C)C=CC=CC=1>[C:2]1([C:1]2[S:33][C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 10870609HCID 10870609, compound

Product 1

HCID 12477826HCID 12477826, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirring solution of ethyl 2-benzoyl-4-oxo-4-phenylbutanoate 69 (0.812 g, 2.62 mmol) in toluene (20 mLs) was added Lawesson's reagent (1.270 g, 3.14 mmol) and the reaction mixture was refluxed for 4 h then concentrated. The crude residue was purified by ISCO (40 g column, 0 to 30% ethyl acetate in hexane) to afford ethyl 2,5-diphenylthiophene-3-carboxylate 70 (0.44 g 55% yield) as a yellow oil. LRMS (ESI): (calc.) 308.09 (found) 309.27 (MH)+

Workup

  1. temperaturethe reaction mixture was refluxed for 4 h
  2. concentrationthen concentrated
  3. customThe crude residue was purified by ISCO (40 g column, 0 to 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-aedc8217ff0c4c658e09a52a38b0209b
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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