Hydrochloric Acid → HCID 131726646, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 8,9-dihydro-5H-benzo[α][7]annulen-5-one (323 g, 2 mol) in nitromethane (620 ml) was treated with DBU (327 g, 2.1 mol) dropwise at such a rate that the temperature was maintained between 40 and 50° C. After GC analysis showed reaction completion, 3M HCl (600 ml) was added and the resulting mixture was extracted with tert-butyl methyl ether (2×500 ml). The combined organic phases were treated with brine (500 ml), dried over MgSO4, filtered and evaporated to an oil (496 g, 90%). To 347.5 g (1.58 mol) of this material dissolved in TFA (1045 ml) was added triethylsilane (583 ml, 3.65 mol) at such a rate that the temperature of the reaction mixture was maintained between 50 and 55° C. After the addition was complete, the mixture was maintained at 55° C. until GC analysis indicated reaction complete. The mixture was poured onto ice (1500 g) and water (500 ml). The resulting slurry was filtered and washed with cold hexanes (2×150 ml) then dried to give the title compound (139 g, 42%).

Provenance & Evidence