Sodium hydride → HCID 54093623, compound

HRID 2290811Notes

Reaction equation

HRID 2290811 reaction equation
[H-].[Na+].[O:3]=[C:4]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:5]P(=O)(OC)OC.[C:18]([O:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[O:30][C:31](=[O:33])[CH3:32])[CH:25]=O)(=[O:20])[CH3:19]>O.C(COC)OC.CS(C)=O>[C:18]([O:21][C:22]1[CH:23]=[C:24]([CH:25]=[CH:5][C:4](=[O:3])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:27]=[CH:28][C:29]=1[O:30][C:31](=[O:33])[CH3:32])(=[O:20])[CH3:19]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 15174883,4-DiacetoxybenzaldehydeHCID 13390134Dimethyl (2-oxooctyl)phosphonate

Product 1

HCID 54093623HCID 54093623, compoundYield 80.4%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent3×

Procedure

To a mixture of 400 mg of oily sodium hydride (60%) and 50 ml of 1,2-dimethoxyethane was added dropwise a mixture of 3.06 g of dimethyl 2-oxooctylphosphonate and 10 ml of dimethoxyethane with stirring under ice-cooling. After adding thereto 5 ml of dimethyl sulfoxide and stirring the mixture for one hour at room temperature, a mixture of 2.22 g of 3,4-diacetoxybenzaldehyde and 10 ml of dimethoxyethane was added dropwise to the mixture. After stirring the resultant mixture for 4 hours at room temperature, 400 ml of water was added to the reaction mixture and the product was extracted twice each time with 50 ml of ether. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was applied to silica gel (120 g) column chromatography and eluted with a mixture of toluene and ethyl acetate (20:1) to provide 2.67 g of 1-(3,4-diacetoxyphenyl)-1-nonen-3-one.

Workup

  1. additionwas added dropwise
  2. temperaturecooling
  3. additionAfter adding
  4. additionwas added dropwise to the mixture
  5. extractionthe product was extracted twice each time with 50 ml of ether
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washeluted with a mixture of toluene and ethyl acetate (20:1)

Sources & evidence

ORD record
ord-e86c48d040f94df2abfc191001038835
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Reaction notes

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