tetraethyl(pyrrolidine-2,2-diyl)bisphosphonate四乙酯(pyrrolidine-2 2-diyl)二磷酸盐.pdfVIP

fulltext Molecules 2001, 6, M275 Tetraethyl(pyrrolidine2,2diyl)bisphosphonate 1* 2 Gilles Olive and Alain Jacques 1 Unité de physique et de chimie des hauts polymères, Université catholique de Louvain, Bâtiment Bolztmann, Place Croix du Sud, 1, B-1348 Louvain-la-Neuve, Belgium, Tel: +32 47 33 91, Fax: +32 45 15 93, e-mail: gilles.olive@ 2 Unité CSTR, Université catholique de Louvain, Bâtiment Lavoisier, Place Louis Pasteur, 1, B-1348 Louvain-la-Neuve, Belgium. E-mail: jacques@chim.ucl.ac.be Received: 1 December 2001 / Accepted: 15 December 2001 / Published: 20 December 2001 Keywords: diphosphorylation, triethylphosphite, pyrrolidone, bisphosphonate. The synthesis of the title compound is already described [1, 2] and we report here the fully optimized procedure. In a double walls flask, under nitrogen, phosphorus oxychloride (20 ml; 0.22 mol) is added for 1 h 00 time to a mixture at -7.5 °C of 2-pyrrolidinone (9.3 g; 0.11 mol) and triethylphosphite (35.1 g; 0.21 mol; 1.9 eq.). The reaction mixture is stirred for 1 hour at room temperature and then poured over a mixture of ice (200 g) and ammonia 30 % (400 ml). The aqueous layer is extracted with methylene chloride (3x100 ml) and then the latter is removed to obtain a yellow oil. The oil is dissolved in 100 ml of methylene chloride. An aqueous solution of hydrochloric acid (10 ml of 32 % HCl solution, 190 ml of water) is added (check that pH 1) and the aqueous layer is washed with methylene chloride (3x100 ml). A solution of sodium hydroxide (20 g of NaOH in 200 ml of water) is added up to pH 10 and the aqueous layer is extracted with methylene chloride (4x100 ml).