Triethyl phosphonoacetate → HCID 86637635, compound

HRID 910006Notes

Reaction equation

HRID 910006 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=1[CH:25]=[CH:26][CH:27]=O>C1COCC1>[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=1[CH:25]=[CH:26][CH:27]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 53429567HCID 53429567, compound

Product 1

HCID 86637635HCID 86637635, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl (diethoxy-phosphoryl)-acetate (3.72 ml, 18.7 mmol) in solution in THF (114 ml) is treated with sodium hydride (60% in oil) (819 mg, 20.4 mmol) at room temperature for 5 minutes. 3-(2,6-Difluoro-phenyl)-propenal (2.87 g, 17.0 mmol) in solution in THF (29 ml) is then added dropwise. After 3 hours of agitation at room temperature, the mixture is evaporated to dryness, taken up in ethyl acetate and washed with water. The organic phase is dried on Na2SO4, filtered and evaporated to dryness. The yellow solid obtained is used directly in the following reaction.

Workup

  1. customthe mixture is evaporated to dryness
  2. washwashed with water
  3. customThe organic phase is dried on Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe yellow solid obtained
  7. customis used directly in the following reaction

Sources & evidence

ORD record
ord-e935fce9a87247c7bb16572f1185cb97
Source dataset
uspto-grants-2011_09
Patent number
US08022064B2

Reaction notes

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