Ammonia → [(2-Aminoethoxy)(3-hydroxyphenyl)methylene]adamantane

Participants

Reaction Conditions

Reaction Steps

##STR37## A solution of alkene 9 (3.0 g, 0.01 mol) in a minimum amount of THF was added into 10 mL of liquid ammonia in a sealed tube which was kept in dry ice. After sealing the tube this was heated at 40° C. in an oil bath for 17 hours. The reaction mixture was cooled down and solvent evaporated to obtain a white solid. This material was extracted with methylene chloride. The combined organic layers were washed with water, dried over MgSO4, and concentrated to give 2.0 g (90%) of alkene 10 as a white solid: mp 55° C., 1H NMR (CDCl3) δ 8 1.77-1.96 (m, 12H), 2.68 (bs, 1H), 2.85 (t, 2H, J=4.8 Hz), 3.23 (bs, 1H), 3.48 (t, 2H, J=4.8 Hz), 4.46 (bs, 2H), 6.70-7.17 (m, 4H); 13C NMR (CDCl3) δ 28.16, 30.28, 32.19, 36.99, 38.88, 39.04, 41.33, 70.45, 114.97, 116.17, 120.63, 129,02, 131.89, 136.69, 141.79, 156.86; MS m/e (rel intensity) 299 (10), 256 (100), 239 (5), 199 (6), 135 (12), 121 (27), 93 (12), 77 (5); MS exact mass: calcd. 299.1885, found 299.1891.

Provenance & Evidence