Methyl iodide → HCID 18177394, compound

HRID 394659Notes

Reaction equation

HRID 394659 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]=[C:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:7][C:6]=2[CH:17]=1.[H-].[Na+].I[CH3:21]>CN(C)C=O.O>[CH3:21][O:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]=[C:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:7][C:6]=2[CH:17]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18177401HCID 18177401, compound

Product 1

HCID 18177394HCID 18177394, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2.8 g (12.75 mmol) of the ester obtained in Step B are dissolved in 30 ml of anhydrous N,N-dimethylformamide. 0.61 g (16 mmol) of sodium hydride is then added slowly to the reaction mixture previously cooled to 0° C. After 30 minutes of stirring under argon and at 0° C., 2.28 g (16 mmol) of iodomethane are added to the reaction medium. After 4 hours of stirring at ambient temperature, the solvent is evaporated in vacuo; the residue obtained is then taken up in water and then extracted with ethyl acetate. The organic phase, dried over magnesium sulphate and then filtered, is concentrated under reduced pressure. The title ester is obtained pure in the form of a white solid after passage over a silica column (eluant: ethyl acetate/petroleum ether: 30/70).

Workup

  1. stirringAfter 4 hours of stirring at ambient temperature
  2. customthe solvent is evaporated in vacuo
  3. customthe residue obtained
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase, dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationis concentrated under reduced pressure

Sources & evidence

ORD record
ord-1d16b7102ef9440785ac95d73bd6da51
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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