Ethyl Acetate → HCID 22678625, compound

HRID 1837691Notes

Reaction equation

HRID 1837691 reaction equation
[CH2:1]([OH:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.[H-].[Na+].[CH2:14]([O:16][CH2:17]Cl)[CH3:15].C(OCC)(=O)C>CN(C)C=O>[CH2:14]([O:16][CH2:17][O:11][CH2:1][C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1)[CH3:15]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10322Piperonyl alcoholHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydride

Product 1

HCID 22678625HCID 22678625, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.56 g of piperonyl alcohol and 1.20 g of 60% sodium hydride were suspended in 30 ml of N,N-dimethylformamide. After stirring for 30 minutes under ice-cooling, 2.28 ml of chloromethyl ethyl ether was added thereto, and the mixture was stirred at room temperature for one hour. Ethyl acetate was added to the reaction solution. The mixture was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by silica gel column chromatography (ethyl acetate:hexane=1:20), to give 4.98 g of the title compound as a colorless oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for one hour
  3. washThe mixture was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe crude product was purified by silica gel column chromatography (ethyl acetate:hexane=1:20)

Sources & evidence

ORD record
ord-25a72358f8f3405f981189e8be414bea
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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