Water → HCID 10083960, compound

HRID 260578Notes

Reaction equation

HRID 260578 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[C:13]([O:15][CH2:16][O:17][CH3:18])=[CH:12][CH:11]=[CH:10]2.[H-].[Na+].[CH3:21]I.O>CN(C)C=O>[CH3:18][O:17][CH2:16][O:15][C:13]1[C:14]2[C:9](=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3][CH2:2][O:1][CH3:21])[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10037558HCID 10037558, compound

Product 1

HCID 10083960HCID 10083960, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.1 g of 8-(3-hydroxypropyl)-1-methoxymethoxy naphthalene was dissolved in 40 ml of N,N-dimethyl formamide, to which 1.4 g of 55% sodium hydride was added under ice cooling. Then, 1.93 ml of methyl iodide was added and stirred at a room temperature for 2 hours. After adding water to the reaction solution and extracting with ethyl acetate, the organic layer was washed with water and then with a saturated aqueous solution of sodium chloride successively and then dried over magnesium sulfate. After distilling off the solvent, when it was purified on silica gel column chromatography (10% ethyl acetate-hexane), 5.3 g of the above-captioned compound was obtained as a colorless oily product.

Workup

  1. additionwas added under ice cooling
  2. extractionextracting with ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialwith a saturated aqueous solution of sodium chloride successively and then dried over magnesium sulfate
  5. distillationAfter distilling off the solvent, when it
  6. customwas purified on silica gel column chromatography (10% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-60c33906516743a4b4546ba976908c06
Source dataset
uspto-grants-1996_06
Patent number
US05527948

Reaction notes

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