Methyl iodide → 1-Methyl-2-oxocycloheptaneacetic acid methyl ester

HRID 1438923Notes

Reaction equation

HRID 1438923 reaction equation
[CH3:1][C:2]1([CH2:10][C:11]([OH:13])=[O:12])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:9].[C:14](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:14][O:12][C:11](=[O:13])[CH2:10][C:2]1([CH3:1])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 12292061HCID 12292061, compound

Product 1

HCID 122919321-Methyl-2-oxocycloheptaneacetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-methyl-2-oxocycloheptaneacetic acid (3.0 g, 0.0163 mole, obtained as described above), anhydrous potassium carbonate (2.76 g, 0.020 mole) and methyl iodide (8 ml) in acetone (50 ml) is stirred and heated to reflux for 2 hrs. Methyl iodide (3ml) is added and heating to reflux is continued for another 3 hrs. The solvent is evaporated, the residue taken up in water (50 ml), saturated with sodium chloride, and extracted with ether. The combined ether extracts are washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated to yield 1-methyl-2-oxocycloheptaneacetic acid methyl ester as an oil, νmaxCHCl3 1730, 1700 cm-1, nmr (CDCl3) δ1.2 (s), 3.67 (s).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hrs
  3. temperatureheating
  4. temperatureto reflux
  5. customThe solvent is evaporated
  6. extractionextracted with ether
  7. washThe combined ether extracts are washed with saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-dcd30a09521346109ee8d55827bf07ac
Source dataset
uspto-grants-1977_11
Patent number
US04057559

Reaction notes

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