Methyl iodide → HCID 19022304, compound

HRID 257671Notes

Reaction equation

HRID 257671 reaction equation
[CH2:1]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[C:16]([O:18]COC)=[C:15]([OH:22])[CH:14]=[CH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:25]I>CN(C)C=O>[CH2:1]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[C:16]([OH:18])=[C:15]([O:22][CH3:25])[CH:14]=[CH:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19022324HCID 19022324, compound

Product 1

HCID 19022304HCID 19022304, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

82.7 g of 8-benzyl-1-methoxymethoxy-2-naphthol was dissolved in 300 ml of N,N-dimethylformamide to give a solution. 12.3 g of sodium hydride (55% suspension in oil) was added to the solution at room temperature. The obtained mixture was stirred for 30 minutes, followed by the dropwise addition of 17.5 ml of methyl iodide. The obtained mixture was stirred for one hour 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, dried over anhydrous magnesium sulfate and concentrated in a vacuum. The obtained residue was purified by silica gel column chromatography (developer: 3 to 9% ethyl acetate/hexane) to give 79.5 g of the title compound as a yellow oil.

Workup

  1. customto give a solution
  2. stirringThe obtained mixture was stirred for one hour
  3. additionpoured onto ice-water
  4. extractionThe obtained mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in a vacuum
  8. customThe obtained residue was purified by silica gel column chromatography (developer: 3 to 9% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ca67f93b5e114302a411fe800fcf6d16
Source dataset
uspto-grants-1993_11
Patent number
US05262565

Reaction notes

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