Water → HCID 18996928, compound

HRID 374416Notes

Reaction equation

HRID 374416 reaction equation
[CH:1]1([C:4]([CH:6]([C:14]([C:16]2[C:17]([S:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:15])C(OC(C)(C)C)=O)=[O:5])[CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.O>C1(C)C=CC=CC=1>[CH:1]1([C:4](=[O:5])[CH2:6][C:14]([C:16]2[C:17]([S:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:15])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 18996925HCID 18996925, compound

Product 1

HCID 18996928HCID 18996928, compoundYield 115.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of t-butyl 2-cyclopropanecarbonyl-3-(2-methylsulphenylpyridin-3-yl)-3-oxopropanoate (9.44 g) and 4-toluenesulphonic acid (0.4 g) in dry toluene was stirred at reflux for 5 hours then allowed to stand at room temperature overnight. The mixture was stirred at reflux for a further 5 hours, cooled to room temperature and taken up into ethyl acetate and water. The phases were separated and the aqueous phase was further extracted with ethyl acetate. The combined organic extracts were dried (anhydrous magnesium sulphate), filtered and evaporated to give 1-cyclopropyl-3-(2-methylsulphenylpyridin-3-yl)propan-1,3-dione (7.64 g) as a brown oil which was used without further purification.

Workup

  1. temperatureat reflux for 5 hours
  2. stirringThe mixture was stirred
  3. temperatureat reflux for a further 5 hours
  4. customThe phases were separated
  5. extractionthe aqueous phase was further extracted with ethyl acetate
  6. dry with materialThe combined organic extracts were dried (anhydrous magnesium sulphate)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-74671f05ad44411aa328aa3f4bc96e6b
Source dataset
uspto-grants-1996_01
Patent number
US05480857

Reaction notes

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