Potassium Carbonate → Dibenzyl ether

Beteiligte Stoffe

Reaktionsschritte

The 2-Methoxy estrone (0.521 g, 0.00173 mol) was dissolved in anhydrous DMF under nitrogen atmosphere, added K2CO3 (0.718 g, 0.00225 mol) and stirred at r.t. for approximately 40 h. The crude mixture was diluted with EtOAc, washed with water and brine. The organics were dried (MgSO4) and concentrated. The crude product was pre-absorbed onto silica gel, purified using Flash Master-2 system to give the benzylated compound 32 (0.651 g, 96%) as a chalky white solid: TLC (Rt, 0.4, EtOAc:Hexane, 3:7); 1H NMR (270 MHz, CDCl3) δ 0.90 (s, 3H, 18-CH3 diastereomeric methyl signals), 1.24-1.27 (t, J=3.4 Hz, 3H, CH2—CH3), 1.24-1.29 (t, J=7.1 Hz, 3H, CH2—CH3), 1.39-2.44 (broad m, 12H), 2.44-2.54 (dd, J=18.8 and 8.6 Hz, 1H), 2.77-2.83 (m, 2H), 3.84-3.87 (s, 3H, OMe), 5.0 (s, 2H, PhCH2), 6.6 (s, 1H, aromatic), 6.77 (s, 1H, aromatic), 3.87-3.84 (s, 3H, OMe), 4.10-4.16 (q, J=7.0 Hz, 2H, CH3—CH2—O), 5.09 (s, 2H, CH2-phenyl), 6.61 (s, 1H, 4-CH), 6.82 (s, 1H, aromatic 1-CH), 7.41-7.43 (m, 5H).

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