Cyclopropyl methyl ketone → 1-Cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)-1,3-propanedione

HRID 1019347Notes

Reaction equation

HRID 1019347 reaction equation
C[O-].[Na+].[CH3:4][S:5][C:6]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:7]=1[C:8]([O:10]C)=O.[CH3:20][C:21]([CH:23]1[CH2:25][CH2:24]1)=[O:22]>CN1CCCC1=O>[CH:23]1([C:21](=[O:22])[CH2:20][C:8]([C:7]2[CH:12]=[CH:13][C:14]([C:16]([F:19])([F:18])[F:17])=[CH:15][C:6]=2[S:5][CH3:4])=[O:10])[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 13004Cyclopropyl methyl ketoneHCID 10942334Sodium MethoxideHCID 10944828Methyl 2-(methylthio)-4-(trifluoromethyl)benzoate

Product 1

HCID 111201781-Cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)-1,3-propanedioneYield 94.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
30 °C

Procedure

Sodium methoxide (0.54 g, 0.01M) was added to a mixture of methyl 2-methylthio-4-trifluoromethylbenzoate (1.25 g. 0.005M) and cyclopropyl methyl ketone (0.5 g, 0,006M) in anhydrous N-methylpyrrolidinone and heated at 30° C. for 3 hours. The cooled mixture was acidified, extracted (ether), washed (Water) and evaporated to give 1-cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)propane-1,3-dione (1.43 g), m.p.68° C. in a yield of 94%. The purity of the product was greater than 95%.

Workup

  1. extractionextracted (ether)
  2. washwashed (Water)
  3. customevaporated

Sources & evidence

ORD record
ord-d01d62b3eda746129c12e8a6784c4e89
Source dataset
uspto-grants-2002_11
Patent number
US06486356B2

Reaction notes

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