Triethyl phosphonoacetate → HCID 21939967, compound

HRID 2269712Notes

Reaction equation

HRID 2269712 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14]CC)=[O:13])(OCC)=O)C.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([CH:32]=O)=[CH:28][CH:27]=2)=[CH:21][CH:20]=1.[OH-].[Na+]>O.C(O)C>[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][C:26]2[CH:27]=[CH:28][C:29](/[CH:32]=[CH:11]/[C:12]([OH:14])=[O:13])=[CH:30][CH:31]=2)=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 13345Triethyl phosphonoacetateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 104895194-(4-Methoxyphenoxy)benzaldehyde

Product 1

HCID 21939967HCID 21939967, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium hydride (60% dispersion in oil; 0.36 g) was added to an ethanol (30 ml) solution of ethyl diethylphosphonoacetate (1.4 g) at room temperature. The reaction mixture was stirred at room temperature for 10 minutes, to which was added 4-[(4-methoxyphenyl)oxy]benzenecarboaldehyde (1.2 g). The reaction mixture was stirred at room temperature for 2 hours, which was further stirred at 50° C. for 30 minutes. The reaction mixture was cooled, to which were added water (20 ml) and sodium hydroxide (0.5 g). The reaction mixture was stirred at room temperature for 2 hours, and concentrated. 2N Hydrochloric acid was added to the residue to become acidic, which was extracted with ethyl acetate. The organic layer was washed with water, then dried and concentrated. The residue was recrystallized from ethyl acetate-hexane to obtain the entitled compound (1.2 g).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. stirringwhich was further stirred at 50° C. for 30 minutes
  3. temperatureThe reaction mixture was cooled, to which
  4. stirringThe reaction mixture was stirred at room temperature for 2 hours
  5. concentrationconcentrated
  6. addition2N Hydrochloric acid was added to the residue
  7. extractionwhich was extracted with ethyl acetate
  8. washThe organic layer was washed with water
  9. customdried
  10. concentrationconcentrated
  11. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2ee1fc82e0894f668d511a7804a98080
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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