ChemicalBook CAS DataBase List Tetraethyl(ethoxycarbonylethylidene)bisphosphonate

Tetraethyl(ethoxycarbonylethylidene)bisphosphonate synthesis

6synthesis methods

Product Name:Tetraethyl(ethoxycarbonylethylidene)bisphosphonate
CAS Number:1112-29-4
Molecular formula:C13H28O8P2
Molecular Weight:374.3

1660-94-2 Synthesis

1660-94-2
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105-36-2 Synthesis

105-36-2
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Tetraethyl(ethoxycarbonylethylidene)bisphosphonate

1112-29-4
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Yield:1112-29-4 73%

Reaction Conditions:

Stage #1: Tetraethyl methylenediphosphonatewith sodium hexamethyldisilazane in tetrahydrofuran at -5;Inert atmosphere;
Stage #2: ethyl bromoacetate in tetrahydrofuran at -5 - 0; for 18 h;Inert atmosphere;

Steps:

General procedure for the synthesis of the bisphosphonates 3-6

General procedure: NaHMDS (1.5 equiv) was added dropwise to a solution of tetraethylmethylene disphosphonate in THF (10 mL) at -5 °C under nitrogen. After that, the respective alkyl halide 7-10 (2.5 equiv),respectively, was added at -5 °C to the previous solution. The reaction mixture was stirred at 0 °Cfor 18 h. Finally, the crude reaction was concentrated, and the crude product was purified by column chromatography (AcOEt:MeOH, 95:05), yielding the bisphosphonates 3-6.

References:

Cortes-Pacheco, Abimelek;Jiménez-Arellanes, María Adelina;Juárez-Vázquez, María del Carmen;López-Torres, Adolfo;Palacios-Can, Francisco José;Ramírez-Marroquín, Oscar Abelardo;Razo-Hernández, Rodrigo Said;Valcarcel-Gami?o, José Antonio [Beilstein Journal of Organic Chemistry,2020,vol. 16,p. 1277 - 1287] Location in patent:supporting information