Lawesson's reagent → HCID 59128210, compound

HRID 1990688Notes

Reaction equation

HRID 1990688 reaction equation
O=[C:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][CH2:4][C:5]([O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1(C)C=CC=CC=1>[CH:8]1([O:7][C:5]2[S:29][C:2]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:3][CH:4]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagent2×HCID 59128209HCID 59128209, compound

Product 1

HCID 59128210HCID 59128210, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 500 mL round-bottomed flask under argon was added cyclohexyl 4-oxo-4-phenylbutanoate (2 g, 7.68 mmol) and Lawesson reagent (3.73 g, 9.22 mmol) in anhydrous toluene (125 mL) to give a white suspension. The mixture was heated to reflux whereby the lawesson's reagent dissolved. The mixture was refluxed for ˜24 h at which point the mixture was cooled and filtered. The filtrate was concentrated and placed on a short column of SiO2 and flashed with CH2Cl2:Hex 1:3 yielding a white solid (1.4 g) which was 2-(cyclohexyloxy)-5-phenylthiophene (70%)

Workup

  1. customto give a white suspension
  2. temperatureThe mixture was heated
  3. dissolutiondissolved
  4. temperatureThe mixture was refluxed for ˜24 h at which point the mixture
  5. temperaturewas cooled
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0d70a569e3234f70a41982337a3b59be
Source dataset
uspto-grants-2010_01
Patent number
US07645558B2

Reaction notes

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