Methyl iodide → HCID 15790490, compound

HRID 1609249Notes

Reaction equation

HRID 1609249 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([OH:15])[CH:10]=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.O1CCC[CH2:17]1.CC(C)([O-])C.[K+].CI>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([O:15][CH3:17])[CH:10]=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 157904882-(4-Chlorophenyl)-1-hydroxy-1H-pyrrole-3-carbonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 15790490HCID 15790490, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 2-(p-chlorophenyl)-1-hydroxypyrrole-3-carbonitrile (2.88 g, 0.0132 mol) and anhydrous tetrahydrofuran is added potassium tert-butoxide (1.55 g, 0.0138 mol). After 30 minutes, methyl iodide (2.06 g, 0.9 mL, 0.0145 mol) is added and the resulting slurry is stirred at room temperature for hours, diluted with water and extracted with ether. The combined ether extracts are washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to yield a solid. Crystallization of the solid from ether/hexanes gives the title compound as a brown solid (2.35 g, 77%), mp 105°-106° C.

Workup

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

Sources & evidence

ORD record
ord-c86c093b6a74496c8890a802be467dc4
Source dataset
uspto-grants-1995_03
Patent number
US05399716

Reaction notes

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