Diethyl ethylphosphonate → Ethyl 3-(ethoxycarbonyl)-3-(ethoxy-ethylphosphinyl)propionate

HRID 374244

Reaction equation

HRID 374244 reaction equation
[C:1]([O:10][CH2:11][CH3:12])(=[O:9])/[CH:2]=[CH:3]/[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:13]([P:15](OCC)(=[O:19])[O:16][CH2:17][CH3:18])[CH3:14]>C(O)C>[CH2:11]([O:10][C:1]([CH:2]([P:15]([O:16][CH2:17][CH3:18])([CH2:13][CH3:14])=[O:19])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:9])[CH3:12]

Participants

4

Reactant 2

HCID 6534Diethyl ethylphosphonateHCID 638144Diethyl fumarate

Product 1

HCID 15052087Ethyl 3-(ethoxycarbonyl)-3-(ethoxy-ethylphosphinyl)propionateYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

172 g of diethyl fumarate are slowly added at 65°-70° C. under nitrogen to a mixture of 140 g of diethyl ethanephosphonate in 46 g of ethanol. After a further 3 hours the solvent (excess ethanol and diethyl ether) is removed by vacuum distillation; the crude product is obtained in a yield of 285 g with a 95.7% purity, which corresponds to a theoretical yield of 90.9%.

Workup

  1. customAfter a further 3 hours the solvent (excess ethanol and diethyl ether) is removed by vacuum distillation

Sources & evidence

ORD record
ord-d0758f6a49c84695af6163c5c5e758e4
Source dataset
uspto-grants-1992_11
Patent number
US05166385

Linked notes

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