Tetrahydrofuran → HCID 67793754, compound

Temperature

0 °C

To a solution of 2-bromo-5-methylene-dibenzo[a,d]cycloheptene (5.7 g) in dry THF (20 ml), under an inert atmosphere, was added 9-borabicyclo[3,3,1]nonane (4.4 ml of a 0.5 molar solution in THF) at ambient temperature, and the reaction mixture was then refluxed for 3 h. After cooling in an ice bath the reaction was quenched by the slow addition of 2N sodium hydroxide solution (100 ml) and 30% hydrogen peroxide (20 ml). After stirring vigorously at 0° C. for 45 minutes the reaction mixture was allowed to warm to room temperature over a 2 h period then extracted with diethyl ether (3×200 ml). The combined organic layers were washed with brine (1×100 ml), dried (Na2SO4), filtered and concentrated in vacuo to leave a residue which was purified by chromatography on flash silica with 30% ethyl acetate in hexane as eluent to give the title compound (6.0 g) as a colourless oil. δ (360 MHz, CDCl3) 3.81 (2H, d, J=7.9 Hz, CH--CH2OH), 4.17 (1H, t, J=7.9 Hz, CH--CH2OH), 6.75 (1H, d, J=12 Hz, CHA =CHB), 6.89 (1H, d, J=12 Hz, CHA =CHB), 7.15-7.48 (7H, m, ArH).

1. temperaturethe reaction mixture was then refluxed for 3 h
2. temperatureAfter cooling in an ice bath the reaction
3. customwas quenched by the slow addition of 2N sodium hydroxide solution (100 ml) and 30% hydrogen peroxide (20 ml)
4. temperatureto warm to room temperature over a 2 h period
5. extractionthen extracted with diethyl ether (3×200 ml)
6. washThe combined organic layers were washed with brine (1×100 ml)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto leave a residue which
11. customwas purified by chromatography on flash silica with 30% ethyl acetate in hexane as eluent

ORD record

ord-6633ff0cc0fd4f358e7a4821ba490145

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04927819