1,2-Dimethoxyethane → HCID 54107578, compound

HRID 569638Notes

Reaction equation

HRID 569638 reaction equation
COCCOC.[H-].[Na+].[O:9]=[C:10]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:11]P(=O)(OC)OC.[CH:23](=O)[C:24]1[CH:33]=[CH:32][C:29]([O:30][CH3:31])=[C:26]([O:27][CH3:28])[CH:25]=1>O>[CH3:28][O:27][C:26]1[CH:25]=[C:24]([CH:23]=[CH:11][C:10](=[O:9])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:33]=[CH:32][C:29]=1[O:30][CH3:31]

Participants

6

Reactant 4

HCID 80711,2-Dimethoxyethane3×HCID 8419VeratraldehydeHCID 24758Sodium hydrideHCID 580181Dimethyl (2-oxoheptyl)phosphonate

Product 1

HCID 54107578HCID 54107578, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under cooling with ice, to 70 ml of dry 1,2-dimethoxyethane containing 0.87 g of sodium hydride (50% mineral oil) was added dropwise 30 ml of dry 1,2-dimethoxyethane containing 4.0 g of dimethyl 2-oxoheptylphosphonate. Then, the mixture was stirred at room temperature for 1 hour and, after that, cooled at -30° C. Then, 3 ml of dry 1,2-dimethoxyethane containing 3.0 g of veratraldehyde was added dropwise. After dropping, the temperature was restored slowly to room temperature. Then, the reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried with magnesium sulfate. The solvent was removed by distillation to obtain crude product. After purification of the crude product by means of column chromatography (silica gel/hexane:ethyl acetate=3:1), 1.3 g of the above caption compound was obtained.

Workup

  1. temperatureafter that, cooled at -30° C
  2. customwas restored slowly to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was removed by distillation
  7. customto obtain crude product
  8. customAfter purification of the crude product by means of column chromatography (silica gel/hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-d9fa24e7b77b413f9104a49bac4fbbb3
Source dataset
uspto-grants-1988_03
Patent number
US04733002

Reaction notes

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