Tetrahydrofuran → HCID 67794827, compound

Temperature

0 °C

To a solution of 2-chloro-5-methylene-dibenzo[a,d]cycloheptene (8.3 g) in dry tetrahydrofuran (30 ml). under an inert atmosphere, was added 9-borabicyclo [3.3.1]nonane (71 ml of a 0.5 molar solution in tetrahydrofuran) at ambient temperature and the reaction mixture was then refluxed for 3 h. After cooling. the reaction was quenched by the slow addition of 2N sodium hydroxide solution (180 ml) and 30% hydrogen peroxide (36 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 into diethyl ether (3×250 ml). The combined organic layers were washed with brine (1×150 ml), dried (Na2SO4), filtered and concentrated in vacuo to leave a residue which was purified by chromatography on flash silica with 40% ethyl acetate in hexane as eluent to give the title compound (8.1 g) as a colourless oil. δ (360 MHz, CDCl3) 3.80 (2H. d, J=7.9 Hz CH--CH2OH), 4.18 (1H, t, J= 7.9 Hz, CH--CH2OH), 6.76 (1H, d, J=11.9 Hz, CHA =CHB) 6.89 (1H, d, J=11.9 Hz, CHA =CHB), 7.24-7.38 (7H, m, ArH); m/e 258 and 256 (M+)

1. temperaturethe reaction mixture was then refluxed for 3 h
2. temperatureAfter cooling
3. customthe reaction was quenched by the slow addition of 2N sodium hydroxide solution (180 ml) and 30% hydrogen peroxide (36 ml)
4. temperatureto warm to room temperature over a 2 h period
5. extractionthen extracted into diethyl ether (3×250 ml)
6. washThe combined organic layers were washed with brine (1×150 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 40% ethyl acetate in hexane as eluent

ORD record

ord-f439622535924c3e964bcadd79772dee

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04927819