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<strong>Synthèse</strong> chimique<br />
1.10.26. <strong>Synthèse</strong> du citrate <strong>de</strong> 1-[4-(3-Hydrodiméthylamoniumpropoxy)phényl]-1-(4-<br />
hydroxyphényl)-2-ferrocényl-but-1-ène, P514<br />
Fe<br />
P15<br />
OH<br />
O(CH 2 ) 3 NMe 2<br />
HO<br />
HOOC<br />
Ether/THF<br />
COOH<br />
COOH<br />
U.P.M.C./U.S. 97<br />
2010<br />
Fe<br />
P514<br />
OH<br />
HO<br />
OOC<br />
O(CH 2) 3NMe 2H<br />
COOH<br />
COOH<br />
Schéma 25 : <strong>Synthèse</strong> du Citrate <strong>de</strong> 1-[4-(3-Hydrodiméthylamoniumpropoxy)phényl]-1-(4-<br />
hydroxyphényl)-2-ferrocényl-but-1-ène<br />
Le produit P15 (0,509 g ; 1 mmol) est dissout dans un ballon contenant 250 ml d’éther sec.<br />
L’aci<strong>de</strong> citrique (0,210 g ; 1 mmol ; 1 eq), préalablement dissout dans du THF est ajouté<br />
goutte à goutte. Un précipité jaune est instantanément formé <strong>et</strong> est isolé par filtration puis<br />
séché à la pompe à vi<strong>de</strong> fournissant P514 en ren<strong>de</strong>ment quantitatif.<br />
P514 contient <strong>de</strong>s traces <strong>de</strong> solvants (THF <strong>et</strong> di<strong>et</strong>hyl <strong>et</strong>her). IR (KBr, �/cm -1 ): 3421 (OH),<br />
3093, 3032, 2966, 2873 (CH2, CH3), 1720 (CO). 1 H NMR (CD3OD) (Z/E � 50/50): � 0.98 (3<br />
H, t, J 7.3 Hz, CH3 for one isomer), 1.00 (3 H, t, J 7.3 Hz, CH3 for one isomer), 2.21 (2 H,<br />
broad m, CH2), 2.60 (2 H, q, J 7.3 Hz, CH2 for one isomer), 2.74 (2 H, d, J 15.3 Hz, CH2),<br />
2.79 (2 H, d, J 15.3 Hz, CH2), 2.85 and 2.86 (6 H, 2 s, NMe2H), 3.24 (2 H, broad m, CH2N),<br />
3.87 (2 H, t, J 1.9 Hz, C5H4 for one isomer), 3.89 (2 H, t, J 1.9 Hz, C5H4 for one isomer), 4.04<br />
(4 H, m, CH2O + C5H4), 4.09 (5 H, s, Cp), 6.61 (2 H, d, Harom for one isomer), 6.73 (2 H, d,<br />
Harom for one isomer), 6.76 (2 H, d, Harom for one isomer), 6.79 (2 H, d, Harom for one isomer),<br />
6.90 (4H, d, Harom), 6.98 (2 H, d, Harom for one isomer), 7.10 (2 H, d, Harom for one isomer).<br />
13 C NMR (CD3OD): � 15.9 (CH3), 25.7 (CH2), 29.1 (CH2), 43.6 (NMe2H + ), 45.3 (CH2), 56.7<br />
(CH2N), 66.1 (CH2O), 68.9 (2 CH, C5H4), 70.1 (5 CH, Cp), 70.3 (2 CH, C5H4), 74.6 (Cq,<br />
citrate), 88.7 (Cipso C5H4), 115.1 (2 CH, C6H4 for one isomer), 115.3 (2 CH, C6H4 for one<br />
isomer), 115.9 (2 CH for one isomer), 116.0 (2 CH, 115.1 (2 CH for one isomer), 131.6 (2<br />
CH, C6H4), 132.2 (2 CH, C6H4), 137.7 (C), 137.8 (C), 138.8 (C), 139.2 (C), 156.9 (C), 158.3<br />
(C), 175.9 (2xCO), 180.3 (CO).
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