Estrone → HCID 22983877, compound

Participants

Reaction Steps

A mixture of estrone (10 g; 37 mmol), Nal (1.1 g, 7.4 mmol), Cs2CO3 (18.08 g; 55.5 mmol) and Br(CH2)2OCH3 (15 mL; 156 mmol) in CH3CN (200 mL) was refluxed for 1 h. The mixture was filtered over silica gel and washed successively with CH2Cl2 and EtOAc to give the ether (12.1 g; 99.4%); 1H NMR (300 MHz, CDCl3) δ 7.23 (d, 1H, J=8.6 Hz), 6.75 (dd, 1H, J=2.6, 8.6 Hz), 6.72 (s, 1H), 4.1 (t, 2H, J=4.4 Hz), 3.74(t, 2H, J=3.7 Hz), 3.44 (s, 3H), 2.87 (dd, 2H, J=4.25, 8.5 Hz), 2.48 (dd, 1H, J=8.4, 18.7 Hz), 0.91 (s, 3H).

Provenance & Evidence