Sodium Iodide → [(3-Hydroxyphenyl)(2-iodoethoxy)methylene]adamantane

Participants

Reaction Steps

##STR36## Sodium iodide (14.0 g, 0.09 mol) and [(2-chloroethoxy)(3-hydroxyphenyl)methylene]adamantahe 8 (3.0 g, 0.009 mol) were dissolved in dry acetone and refluxed for 6 days. The reaction was followed by TLC analysis (ethyl acetate/hexane, 10:90) and after the completion of reaction, solvent was evaporated to obtain a white solid. This solid was washed with methylene chloride several times and the combined organic layers were again washed with water. The organic layer was dried over MgSO4 and concentrated to give 3.8 g (100%) of alkene 9 as an oily material: 1H NMR (CDCl3) δ 1.78-1.97 (m, 12H), 2.64 (bs, 1H), 3.19 (t, 2H, J=7.1 Hz), 3.35 (bs, 1H), 3.69 (t, 2H, J=7.1 Hz), 6.75-7.21 (m, 4H); 13C NMR (CDCl3) δ 2.40, 28.13, 30.41, 32.33, 36.99, 38.86, 39.09, 69.74, 114.86, 116.00, 121.79, 129.28, 133.37, 136.42, 140.51, 155.66; MS m/e (rel intensity) 410 (42), 256 (19), 227 (75), 155 (18), 121 (100), 107 (32), 93 (28), 79 (14), 65 (16); MS exact mass:calcd. 410.0744, found 410.0744.

Provenance & Evidence