Triethyl phosphonoacetate → HCID 59859880, compound

HRID 1072713Notes

Reaction equation

HRID 1072713 reaction equation
[CH2:1]([C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C(OP([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(OCC)=O)C.[H-].[Na+]>C1COCC1>[CH2:1]([C:6]1[CH:13]=[CH:12][C:9](/[CH:10]=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 23290Benzaldehyde, 4-pentyl-HCID 24758Sodium hydride

Product 1

HCID 59859880HCID 59859880, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-pentylbenzaldehyde (25 g, 142 mmol) and ethyl diethylphosphonoacetate (30 ml, 150 mmol) in THF was added sodium hydride (60%, 6 g, 150 mmol), and the mixture was stirred at room temperature for 12 hours and poured into ice water. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate anhydride, and the solvent was removed under reduced pressure to give the object compound as an oily substance. 39.6 g, (yield 100%)

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate anhydride
  4. customthe solvent was removed under reduced pressure
  5. customto give the object compound as an oily substance

Sources & evidence

ORD record
ord-eeb7effb039047349cf3e2f32766bb51
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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