Triethyl phosphonoacetate → HCID 86749011, compound

HRID 2400159Notes

Reaction equation

HRID 2400159 reaction equation
[H-].[Na+].[CH2:3]([O:5][P:6]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])([O:8][CH2:9][CH3:10])=[O:7])[CH3:4].[CH2:17](Br)[CH:18]=[C:19]([CH2:21][CH2:22][CH:23]=[C:24]([CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])[CH3:25])[CH3:20]>CN(C)C=O>[C:12]([CH:11]([P:6](=[O:7])([O:5][CH2:3][CH3:4])[O:8][CH2:9][CH3:10])[CH2:17]/[CH:18]=[C:19](\[CH3:20])/[CH2:21][CH2:22]/[CH:23]=[C:24](\[CH3:25])/[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 550199Farnesyl bromide

Product 1

HCID 86749011HCID 86749011, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

0.59 g of 55% sodium hydride was suspended in 5 ml of N,N-dimethylformamide in a nitrogen atmosphere, followed by the dropwise addition thereto of 5 ml of a solution of 3.0 g of ethyl diethylphosphonoacetate in N,N-dimethylformamide at room temperature. The obtained mixture was stirred for 10 minutes. 5 ml of a solution of 4.5 g of farnesyl bromide in N,N-dimethylformamide was added to the resulting mixture at room temperature. The obtained mixture was further stirred for one hour, followed by the addition thereto of ice-water. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and distilled in a vacuum to remove the solvent. The obtained crude product was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to give 2.6 g of the title compound as a colorless oil.

Workup

  1. additionfollowed by the dropwise addition
  2. customat room temperature
  3. stirringThe obtained mixture was further stirred for one hour
  4. additionfollowed by the addition
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous solution of common salt
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationdistilled in a vacuum
  9. customto remove the solvent
  10. customThe obtained crude product
  11. customwas purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-52259956dc9b4945ab8b48f44eec31ae
Source dataset
uspto-grants-1995_09
Patent number
US05453524

Reaction notes

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