反应详情

Bromo-2-propenyl-magnesium (0.0542 mol) was added dropwise to a solution of intermediate 2 (0.04956 mol) in tetrahydrofuran(120 ml) under N2 atmosphere. The reaction mixture was stirred for 30 minutes at room temperature, then stirred and refluxed for 2 hours. The reaction mixture was cooled on an ice-bath, quenched with a 20% NH4Cl solution, and extracted with ethylacetate. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified and separated into two regio-isomers by HPLC over silica gel (eluent: hexanes/ethylacetate 9/1). Two pure fraction groups were collected and their solvent was evaporated, yielding 4.79 g (36%) of (±)-trans-8-fluoro-10,11-dihydro-11-(2-propenyl)-5H-dibenzo [a,d]cyclohepten-10-ol (intermediate 3) and 2.52 g (19%) of (trans)-2-fluoro-10,11-dihydro-11-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-10-ol (intermediate 4).

1. stirringstirred
2. temperaturerefluxed for 2 hours
3. temperatureThe reaction mixture was cooled on an ice-bath
4. customquenched with a 20% NH4Cl solution
5. extractionextracted with ethylacetate
6. customThe organic layer was separated
7. customdried
8. filtrationfiltered
9. customthe solvent was evaporated
10. customThe residue was purified
11. customseparated into two regio-isomers by HPLC over silica gel (eluent: hexanes/ethylacetate 9/1)
12. customTwo pure fraction groups were collected
13. customtheir solvent was evaporated