Lawesson's reagent → 2-Cyclohexyl-5-(5-methylthiophen-2-yl)thiophene

HRID 236560Notes

Reaction equation

HRID 236560 reaction equation
[C:1]1([C:7](=O)[CH2:8][CH2:9][C:10]([C:12]2[S:13][C:14]([CH3:17])=[CH:15][CH:16]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>C1(C)C=CC=CC=1>[CH3:17][C:14]1[S:13][C:12]([C:10]2[S:28][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][CH:9]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 135558071-Phenyl-4-(5-methyl-2-thienyl)-1,4-butanedione

Product 1

HCID 1847532-Cyclohexyl-5-(5-methylthiophen-2-yl)thiopheneYield 131.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere a stirred solution of 3.0 grams (0.012 mole) of 1-phenyl-4-(5-methyl-2-thienyl)-1,4-butanedione and 3.0 grams (0.008 mole) of Lawesson's reagent in 100 ml of toluene was heated under reflux for one hour. The reaction mixture was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel using 15% methylene chloride-hexane as eluent. The appropriate fractions were combined and concentrated under reduced pressure to give 2.7 grams of 5'-methyl-5-phenyl[2,2'-bithienyl]; m.p. 102° C.

Workup

  1. temperatureunder reflux for one hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure to a residue
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0326d704da4f4ca183d7e8cd6f89f26c
Source dataset
uspto-grants-1987_02
Patent number
US04645777

Reaction notes

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