Triethyl phosphonoacetate → HCID 67244312, compound

HRID 2423343Notes

Reaction equation

HRID 2423343 reaction equation
C([O:3][C:4](=[O:14])[CH2:5]P(OCC)(OCC)=O)C.[H-].[Na+].[C:17]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](C2C=CC=CC=2)=O)=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([C:27]([CH3:28])=[CH:5][C:4]([OH:3])=[O:14])=[CH:25][CH:26]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 9837898HCID 9837898, compound

Product 1

HCID 67244312HCID 67244312, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

The solution of ethyldiethylphosphonoacetate (1.2 eq, 0.25 g) in 4 ml of DMF was put into the flask and then cooled to 0° C. To the solution was added 60% sodium hydride (1.4 eq, 1.27 mmol, 51 mg) and then added 4-t-butylphenylacetophenone (0.16 g, 0.91 mmol) in 3 ml DMF slowly. The mixture solution was stirred for 4 hours. After conforming the completion of the reaction with TLC, the reaction mixture was extracted with ethylacetate, and washed with water. The combined organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The obtained liquid was dissolved in MeOH/THF solution and added 1N NaOH solution, and then refluxed overnight. After conforming the completion of the reaction with TLC, the reaction mixture was extracted with ethylacetate, and acidified with 1N HCl solution. And the combined organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The obtained solid was purified with column chromatography to yield the title compound (134 mg, 68.1%)

Workup

  1. customthe completion of the reaction with TLC
  2. extractionthe reaction mixture was extracted with ethylacetate
  3. washwashed with water
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe obtained liquid was dissolved in MeOH/THF solution
  8. additionadded 1N NaOH solution
  9. temperaturerefluxed overnight
  10. customthe completion of the reaction with TLC
  11. extractionthe reaction mixture was extracted with ethylacetate
  12. dry with materialAnd the combined organic layer was dried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure
  15. customThe obtained solid was purified with column chromatography

Sources & evidence

ORD record
ord-f705e3a516d1454fa00a607dc6c655a1
Source dataset
uspto-grants-2011_06
Patent number
US07960584B2

Reaction notes

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