Reaktion #347381

Reaktionsgleichung

Estradiol

nicotinoyl chloride hydrochloride

→

Estra-1,3,5(10)-triene-3,17β-diol 3,17-dinicotinate

Ausbeute 90.0%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed for 1 hour
2. 2
   Filtrationfiltered
3. 3
   Trocknendried over P2O5 under vacuum

Vorschrift

Estradiol (2 g, 0.0073 mol) was added to nicotinoyl chloride hydrochloride (5.3 g, 0.029 mol) in dry pyridine (30 ml) at 0° C. The mixture was refluxed for 1 hour and then poured over 100 ml of ice water, filtered and dried over P2O5 under vacuum. Yield 90% (3.18 g), m.p. 148°-150° C. NMR (CDCl3) δ 9.2-9.0 (br s, 2H, C2 pyridinium protons), 8.7-8.3 (m, 2H, C6 pyridinium protons), 8.4-8.0 (m, 2H, C4 pyridinium protons), 7.5-7.1 (m, 3H, C5 pyridinium protons+C1 estradiol proton), 6.9-6.7 (m, 2H, C2,4 estradiol protons), 5.0-4.7 (m, 1H, C17α estradiol proton), 3.2-1.3 (estradiol skeletal protons, 15), 1.0-0.9 (s, 3 H, C18 estradiol protons). IR (KBr) 1750, 1725 cm-1 (2 C=O stretching). Anal. calculated for C30H31N2O4 : C, 74.50; H, 6.47; N, 5.79. Found: C, 74.40; H, 6.32; N, 5.75. The product has the formula: ##STR1471##

Quelle