Allyl Alcohol → Allyl P,P-diethylphosphonoacetate

HRID 1452432

Reaction equation

HRID 1452432 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]([OH:12])=[O:11])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[CH2:13](O)[CH:14]=[CH2:15].Cl.C(N=C=NCCCNC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:7]([O:6][P:4]([CH2:9][C:10]([O:12][CH2:15][CH:14]=[CH2:13])=[O:11])([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

6

Reactant 3

HCID 7858Allyl AlcoholHCID 36704(Diethoxyphosphinyl)acetic acidHCID 9794023N-(3-methylaminopropyl)-N'-ethylcarbodiimide hydrochloride

Product 1

HCID 4583084Allyl P,P-diethylphosphonoacetateYield 82.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

29.2 g of the diethylphosphonoacetic acid thus obtained was dissolved in 350 ml of methylene chloride, and 17.8 g of allyl alcohol, 1.92 g of 4-dimethylaminopyridine and 29.0 g of 1-ethyl-3-(3-methylaminopropyl)carbodiimide hydrochloride were added thereto with stirring under cooling with ice. The mixture was stirred at room temperature overnight. The reaction solution was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, then sequentially washed with 1N hydrochloric acid, water, a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and then the solvent was distilled off under reduced pressure to obtain 28.9 g of allyl diethylphosphonoacetate.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe mixture was stirred at room temperature overnight
  3. customThe reaction solution was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washsequentially washed with 1N hydrochloric acid, water
  6. dry with materiala saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  7. customThe drying agent was separated by filtration
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-76f15d3f7acd412ba981e865e2ec841a
Source dataset
uspto-grants-1997_02
Patent number
US05606101

Linked notes

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