Methyl iodide → HCID 19022329, compound

HRID 257674Notes

Reaction equation

HRID 257674 reaction equation
[CH2:1]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[C:16]([OH:18])=[CH:15][CH:14]=[CH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:21]I>CN(C)C=O>[CH2:1]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[C:16]([O:18][CH3:21])=[CH:15][CH:14]=[CH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19022350HCID 19022350, compound

Product 1

HCID 19022329HCID 19022329, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 g of 8-benzyl-1-naphthol was dissolved in 300 ml of N,N-dimethylformamide to give a solution. 24.2 g of sodium hydride (55% suspension in oil) was added to the solution under cooling with ice. The obtained mixture was stirred at room temperature for 30 minutes. Methyl iodide was added to the resulting mixture under cooling with ice. The obtained mixture was stirred for 30 minutes under cooling with ice and poured onto ice-water. The obtained mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride twice, dried over anhydrous magnesium sulfate and distilled in a vacuum to remove the solvent. The residue was purified by silica gel column chromatography (developer: 5% ethyl acetate/hexane) to give 73 g of the title compound.

Workup

  1. customto give a solution
  2. temperatureunder cooling with ice
  3. temperatureunder cooling with ice
  4. stirringThe obtained mixture was stirred for 30 minutes
  5. temperatureunder cooling with ice
  6. additionpoured onto ice-water
  7. extractionThe obtained mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with a saturated aqueous solution of sodium chloride twice
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationdistilled in a vacuum
  11. customto remove the solvent
  12. customThe residue was purified by silica gel column chromatography (developer: 5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-625745ad27d042fa91a0baee40fb1f32
Source dataset
uspto-grants-1993_11
Patent number
US05262565

Reaction notes

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