Anisole → p-Anisyl thiophen-2-yl ketone

HRID 1857125Notes

Reaction equation

HRID 1857125 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1([C:14](Cl)=[O:15])[S:13][CH:12]=[CH:11][CH:10]=1.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[N+](C)([O-])=O>[S:13]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:14]([C:4]1[CH:5]=[CH:6][C:1]([O:7][CH3:8])=[CH:2][CH:3]=1)=[O:15]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 789282-Thiophenecarbonyl chlorideHCID 2733225Ytterbium triflate

Product 1

HCID 77812p-Anisyl thiophen-2-yl ketoneYield 44.2%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To commercially available nitromethane (10 ml) were added commercially available anisole (1.081 g), commercially available 2-thenoyl chloride (1.466 g) and commercially available ytterbium(III) trifluoromethanesulfonate (620 mg), and the admixture was stirred at 60° C. for 8 hours. The reaction mixture was treated in the same manner as described in Example 35 to obtain 965 mg of the title compound (yield: 44%).

Workup

  1. additionThe reaction mixture was treated in the same manner

Sources & evidence

ORD record
ord-1add91d460ff420ba0f56a1cd4482903
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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