Methyl iodide → NSC666539

HRID 240297Notes

Reaction equation

HRID 240297 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=O)O1.[C:11](=[O:14])([O-:13])[O-].[K+].[K+].[CH3:17]I>C(#N)C.ClCCl>[CH3:10][C:2]1([CH3:1])[O:13][C:11](=[O:14])[C:6]([CH3:17])([CH3:4])[C:7](=[O:8])[O:9]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 380817NSC666539

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of Meldrum's acid (5.52 g, 38.3 mmol), potassium carbonate (26.5 g, 191 mmol) and methyl iodide (7.15 mL, 115 mmol) in acetonitrile (75 mL) was heated at 75° C. in a sealed tube for 7 hrs. The mixture was cooled to room temperature, diluted with dichloromethane (300 mL), filtered and the filtrate evaporated to dryness in vacuo. Ethyl acetate (75 mL), hexanes (75 mL) and water (50 mL) were added and phases were separated. The organic layer was washed with 10% aqueous solution of sodium thiosulfate (50 mL) and water (50 mL); dried over anhydrous magnesium sulfate and solvent removed in vacuo to give 2,2,5,5-tetramethyl-[1,3]dioxane-4,6-dione as white solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. customthe filtrate evaporated to dryness in vacuo
  4. additionEthyl acetate (75 mL), hexanes (75 mL) and water (50 mL) were added
  5. customphases were separated
  6. washThe organic layer was washed with 10% aqueous solution of sodium thiosulfate (50 mL) and water (50 mL)
  7. dry with materialdried over anhydrous magnesium sulfate and solvent
  8. customremoved in vacuo

Sources & evidence

ORD record
ord-e1085941cfd24ae9aaaf89254e77a40b
Source dataset
uspto-grants-2014_02
Patent number
US08648041B2

Reaction notes

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