Methyl iodide → HCID 19022362, compound

HRID 257673Notes

Reaction equation

HRID 257673 reaction equation
[CH2:1]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[C:16]([O:18]COC)=[CH:15][CH:14]=[CH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22]N(C)CCN(C)C.C([Li])CCC.CI.[Cl-].[NH4+]>CCOCC.CCCCCC>[CH2:1]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[C:16]([OH:18])=[C:15]([CH3:22])[CH:14]=[CH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 25517Ammonium ChlorideHCID 19022307HCID 19022307, compoundHCID 178418339Butyllithium

Product 1

HCID 19022362HCID 19022362, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

10 g of 8-benzyl-1-methoxymethoxynaphthalene was dissolved in 100 ml of anhydrous ether, followed by the addition of 6.5 ml of tetramethylethylenediamine. 27 ml of a 1.6 M solution of n-butyllithium in hexane was dropped into the obtained mixture under cooling with ice. The obtained mixture was stirred at 0° C. for one hour, followed by the dropwise addition of 2.7 ml of methyl iodide. The obtained mixture was stirred at room temperature for one hour and poured into a saturated aqueous solution of ammonium chloride. The obtained mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and distilled in a vacuum to remove the solvent. The residue was dissolved in 150 ml of acetone, followed by the addition of 60 ml of 6N hydrochloric acid. The obtained mixture was stirred at room temperature for one hour, followed by the addition of water. The obtained mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and distilled in a vacuum to remove the solvent. The residue was purified by silica gel column chromatography (developer: 3% ethyl acetate/hexane) to give 6 g of the title compound as a yellow oil.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe obtained mixture was stirred at room temperature for one hour
  3. extractionThe obtained mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationdistilled in a vacuum
  6. customto remove the solvent
  7. dissolutionThe residue was dissolved in 150 ml of acetone
  8. additionfollowed by the addition of 60 ml of 6N hydrochloric acid
  9. stirringThe obtained mixture was stirred at room temperature for one hour
  10. additionfollowed by the addition of water
  11. extractionThe obtained mixture was extracted with ethyl acetate
  12. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  13. distillationdistilled in a vacuum
  14. customto remove the solvent
  15. customThe residue was purified by silica gel column chromatography (developer: 3% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-24c2134413434ba59c36ba703d104157
Source dataset
uspto-grants-1993_11
Patent number
US05262565

Reaction notes

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