Dimethylformamide → HCID 68431167, compound

HRID 384145Notes

Reaction equation

HRID 384145 reaction equation
[I:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)[OH:9])=[CH:4][CH:3]=1.[H-].[Na+].[Cl-].[NH4+].[CH3:24]N(C)C=O>IC>[I:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)[O:9][CH3:24])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 68428333HCID 68428333, compound

Product 1

HCID 68431167HCID 68431167, compound

Reagents, catalysts & solvents 1

HCID 6328Methyl iodideSolvent

Procedure

To a solution of 2-(4-iodophenoxy)-1-(3-methoxyphenyl)ethanol (215 mg) in dimethylformamide (2 ml), 0.072 ml of iodomethane and 46 mg of sodium hydride were added under ice-cooling, and the reaction solution was stirred at room temperature for 30 minutes. To the reaction solution was added an aqueous saturated ammonium chloride solution, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50/50)) to afford the title compound as a colorless oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with a saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50/50))

Sources & evidence

ORD record
ord-6086a6ea367446a9860be3dabc4430e0
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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