Methyl iodide → HCID 15766625, compound

HRID 2253798Notes

Reaction equation

HRID 2253798 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]([OH:19])[CH:17]=[C:16]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:15]=2)=[CH:10][CH:9]=1.CI>O1CCCC1.O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:18]([O:19][CH3:1])[CH:17]=[C:16]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:15]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 15766624HCID 15766624, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15766625HCID 15766625, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (4.32 g, 0.0385 mol) is added portionwise to a 0° C. solution of ethyl 5-(p-chlorophenyl)-1-hydroxypyrrole-3-carboxylate (9.3 g, 0.035 mol) in anhydrous tetrahydrofuran. Methyl iodide (5.46 g, 0.0385 mol) is then added slowly to the solution at room temperature. The reaction mixture is stirred for 3 hours, diluted with water and extracted with ether. The combined ether extracts are washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give a solid. Crystallization from hexanes gives the title compound as a white crystalline solid (9.25 g, 94%), mp 65°-66° C.

Workup

  1. extractionextracted with ether
  2. washThe combined ether extracts are washed sequentially with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a solid
  6. customCrystallization from hexanes

Sources & evidence

ORD record
ord-cda45285199341cea802509c0bebcb43
Source dataset
uspto-grants-1993_08
Patent number
US05232979

Reaction notes

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