Sodium hydride → 5,5-Diethoxy-3-(3,4-methylenedioxyphenyl)pentan-2-one

HRID 2287500Notes

Reaction equation

HRID 2287500 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11](=[O:13])[CH3:12])=[CH:4][C:3]=2[O:2]1.[H-].[Na+].[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20]I)[CH3:17]>CN(C)C=O>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][CH:10]([C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)[C:11](=[O:13])[CH3:12])[CH3:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 784073,4-Methylenedioxyphenyl-2-propanoneHCID 125047911,1-Diethoxy-2-iodoethane

Product 1

HCID 187052415,5-Diethoxy-3-(3,4-methylenedioxyphenyl)pentan-2-oneYield 94.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 11.7 g of 3,4-methylenedioxyphenylacetone in 100 ml of dimethylformamide, 2.76 g of 60% oily sodium hydride was added under cooling with ice with stirring, and after stirring at the same temperature for 30 minutes, 20.9 g of iodoacetaldehyde diethyl acetal in 20 ml of dimethylformamide was added. The reaction solution was stirred at room temperature for 2 hours and partitioned between water and ethyl ether. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=15/1→10/1] to give 18.3 g of the title compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringafter stirring at the same temperature for 30 minutes
  3. stirringThe reaction solution was stirred at room temperature for 2 hours
  4. custompartitioned between water and ethyl ether
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe desiccant was filtered off
  8. customthe solvent was evaporated in vacuo
  9. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=15/1→10/1]

Sources & evidence

ORD record
ord-942061b64106458396636dc60deae89d
Source dataset
uspto-grants-2000_07
Patent number
US06083985

Reaction notes

Loading…