Iodoethane → HCID 69884098, compound

Participants

Reaction Steps

A solution of 3,17β-bis(methoxymethoxy)estra-1,3,5-triene-2-ol (Z. Wang and Cushman, Synzthetic Commun. 28:4431-4437 (1998)) (11.3 g, 27.8 mmol) in anhydrous ethanol (225 ml) containing anhydrous potassium carbonate (38.4 g, 280 mmol) was stirred at room temperature under argon for 10 min. Iodoethane (43.7 g, 280 mmol) was introduced to the reaction mixture. The resulting mixture was stirred at gentle reflux. After 4 hr, another portion of iodoethane (10.92 g, 70 mmol) was introduced and the reflux was continued for another 10 hr. The reaction mixture was cooled to room temperature and filtered. The solid was washed with ether (100 ml), and the filtrates were combined and evaporated to dryness. Chromatography of the residue (silica gel 230-400 mesh, ethyl acetate:hexane 1:7 by volume) gave the pure 2 (10.45 g, 92%) as a colorless oil: 1H NMR (CDCl3) δ6.85 (s, 2 H), 5.18 (s, 2 H), 4.66 (ABq, J=6.6 Hz, Δν=3.4 Hz, 2 H), 4.08 (q, J=7.0 Hz, 2 H), 3.61 (t, J=8.5 Hz, 1 H), 3.52 (s, 3 H), 3.38 (s, 3 H), 2.79 (m, 2 H), 2.30-1.20 (m, 13 H), 0.82 (s, 3 H); CIMS (isobutane) m/z (rel intensity) 405 (MH+, 39), 343 (100). Anal. Calcd. for C24H37O5: C, 71.26; H, 8.97. Found: C, 71.48; H, 9.14.

Provenance & Evidence