Hydrochloric Acid → HCID 66999647, compound

Participants

Reaction Steps

To a solution of 7-bromo-1-methyldibenz[b,f][1,4]oxazepine (25.05 g, 86.98 mmol) and Ytterbium(III) triflate (2.8 g, 4.5 mmol) in toluene (0.21 L) at 0° C., (E)-1-methoxy-3-trimethylsilyloxy-1,3-butadiene (18 mL, 95.7 mmol) was added dropwise. THF (0.1 L) was added to dissolve the formed precipitate and the solution was stirred for 15 min. 1N hydrochloric acid (50 mL) was added and the resulting mixture was stirred for an additional 15 min, after which it was diluted with ethyl acetate and washed with brine. After drying (Na2SO4) the solvent was evaporated under reduced pressure to yield the crude compound which was triturated in methanol to give the title compound (25.4 g, 82%). Data: 1H-NMR (400 MHz, CDCl3) δ 2.31 (s, 3H), 2.43 (m, 1H), 3.00 (m, 1H), 5.23 (m, 1H), 5.41 (m, 1H), 6.99-7.52 (m, 7H). (m/z)=356+358 (M+H)+.

Provenance & Evidence