Methyl iodide → HCID 22402925, compound

HRID 259678Notes

Reaction equation

HRID 259678 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:17]=[CH:16][C:7]2[C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[N:9][O:10][C:6]=2[CH:5]=1.[CH3:18]I>O1CCCC1>[F:3][C:4]1[CH:17]=[CH:16][C:7]2[C:8]([CH:11]([CH3:18])[C:12]([O:14][CH3:15])=[O:13])=[N:9][O:10][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22402921HCID 22402921, compound

Product 1

HCID 22402925HCID 22402925, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2 °C

Procedure

Sodium hydride (2.32 g, 57.9 mmol, 60% in oil) is added portionwise to a solution of methyl 6-fluoro-1,2-benzisoxazole-3-acetate (12.07 g, 57.7 mmol) in tetrahydrofuran at -2° C. The mixture is stirred for 30 minutes at 2° C., treated with methyl iodide (10.65 g, 75.0 mmol), stirred at 5° C. for 50 minutes and poured onto ice. The aqueous mixture is extracted with methylene chloride. The organic extracts are combined, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title product as an oil which is identified by NMR spectral analyses.

Workup

  1. stirringstirred at 5° C. for 50 minutes
  2. additionpoured onto ice
  3. extractionThe aqueous mixture is extracted with methylene chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-843321cd9b2f4bc8b47a6eb296b57728
Source dataset
uspto-grants-1996_06
Patent number
US05523278

Reaction notes

Loading…