Methyl iodide → HCID 66914819, compound

HRID 880465Notes

Reaction equation

HRID 880465 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[CH:7]([C:10]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]([OH:18])=[O:17])[CH:11]=1)([CH3:9])[CH3:8].CI>CC(C)=O>[CH:7]([C:10]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]([O:18][CH3:1])=[O:17])[CH:11]=1)([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66914731HCID 66914731, compound

Product 1

HCID 66914819HCID 66914819, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Potassium carbonate (298 mg, 2.15 mmol) was added to a solution of 2-(3-isopropylpyrrol-1-yl)acetic acid (180 mg, 1.07 mmol) in acetone at 0° C. and the reaction was stirred at 0° C. for 15 min. Methyl iodide (0.13 mL, 2.15 mmol) was added at 0° C. and the mixture refluxed for 16 h. The reaction mixture was concentrated in vacuo and the residue was diluted with water and extracted with diethyl ether. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to give the crude compound. Purification by column chromatography over neutral alumina by using 1-2% ethyl acetate in petroleum ether as eluent afforded methyl 2-(3-Isopropylpyrrol-1-yl)acetate (135 mg, 69%) as a liquid.

Workup

  1. temperaturethe mixture refluxed for 16 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with diethyl ether
  5. washThe organic layer was washed with water, brine solution
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give the crude compound
  10. customPurification by column chromatography over neutral alumina

Sources & evidence

ORD record
ord-dc4b6c7d5edd429e8e87c04e0ec23dc0
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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