Acetone → HCID 60091526, compound

HRID 353221Notes

Reaction equation

HRID 353221 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:14])[CH2:7][C:8](=[S:13])[O:9][CH:10]([CH3:12])[CH3:11].[C:15](=O)([O-])[O-].[K+].[K+].CC(C)=O.CI>C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:14])/[CH:7]=[C:8](/[O:9][CH:10]([CH3:11])[CH3:12])\[S:13][CH3:15]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 20735499HCID 20735499, compound

Product 1

HCID 60091526HCID 60091526, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of isopropyl 3-(2-furyl)-3-oxopropanethioate (3.7 g, 17.5 mmol), potassium carbonate (7.3 g, 52.4 mmol) and acetone (15 mL) was heated under reflux for 1 hour. After cooling the mixture to 0° C., methyl iodide (2.17 mL, 34.9 mmol) was added thereto, followed by stirring at room temperature for 2 hours. After diluting the reaction solution with ethyl acetate, the insoluble matters were filtered off. The filtrate was concentrated, and then the residue was purified by silica gel column chromatography (elution solvent; ethyl acetate/hexane=1:1), to give the title compound (3.2 g, 81%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. filtrationthe insoluble matters were filtered off
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography (elution solvent; ethyl acetate/hexane=1:1)

Sources & evidence

ORD record
ord-b7b3d27b5f964b0ab3a1c0fad4f83037
Source dataset
uspto-grants-2004_06
Patent number
US06750232B2

Reaction notes

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