Hydrochloric Acid → HCID 131726646, compound

Temperature

55 °C

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%).

1. temperaturewas maintained between 40 and 50° C
2. additionwas added
3. extractionthe resulting mixture was extracted with tert-butyl methyl ether (2×500 ml)
4. additionThe combined organic phases were treated with brine (500 ml)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated to an oil (496 g, 90%)
8. temperaturewas maintained between 50 and 55° C
9. additionAfter the addition
10. customreaction complete
11. filtrationThe resulting slurry was filtered
12. washwashed with cold hexanes (2×150 ml)
13. customthen dried

ORD record

ord-b8afcef92cb2483d83d6fcadd1947fe0

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07285563B2