Preparation of 3,7-Bis(2-hydroxyethyl)icaritin
i would like make this preparation at home using chemicals that are available to the general public : Preparation of
3,7-Bis(2-hydroxyethyl)icaritin Potent Inhibition of Human Phosphodiesterase-5 by Icariin Derivatives
A stirred suspension of icariin 95% (250 mg, 0.7 mmol), 2-bromoethanol (210 mg, 1.7 mmol), and anhydrous K2CO3 (240 mg, 1.7 mmol) in dry acetone (75
mL) was refluxed for 8 h. The hot reaction mixture was filtered, and the solvent was evaporated under reduced pressure. The residue was purified by
flash column chromatography on silica gel (CH2Cl2/acetone, 9:1) and crystallized from EtOH to give the desired compound as a yellow crystalline powder
(70 mg, purity 96.0%); 20.2% yield; mp 152−153 °C; 1H NMR (CDCl3, 300 MHz, 30 °C) δ 1.77 (3H, s, CH3-14), 1.87 (3H, s, CH3-15), 3.61 (2H,
d, J = 6.8 Hz, H-11), 3.78−3.83 (2H, m, 7-OCH2O), 3.90 (3H, s, OCH3), 3.95−4.05 (4H, m, CH2OH), 4.15−4.22 (2H, m, OCH2O-3), 5.19
(1H, t, J = 6.8 Hz, H-12), 6.32 (1H, s, H-6), 7.04 (2H, d, J = 8.4 Hz, H-3′, H-5′ , 8.16 (2H, d, J = 8.4 Hz, H-2′, H-6′; ESIMS (positive-ion
mode) m/z 479 [M + Na]+; anal. C 65.82%, H 6.22%, calcd for C25H28O8, C 65.78%, H 6.18%.
[Edited on 29-7-2009 by mr4563f2]
[Edited on 29-7-2009 by mr4563f2]
[Edited on 29-7-2009 by mr4563f2]
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