Tributylphosphine → [2-(3-Butenyloxy)ethyl]benzene

To a solution of 4-[2-phenylethoxy]butanol (3.16 g) and 2-nitrophenyl selenocyanate (4.0 g) in THF (50 ml) under argon was added tributylphosphine (4.5 ml) in THF (2 ml) dropwise over 30 min. After a further 2 hours at room temperature the solvent was removed under reduced pressure. A further 50 ml of THF was added and the mixture cooled to 0° at which point H2O2 (17 ml, 30% aqueous v/v) was added to the stirred solution over 1 hour. The mixture was allowed to warm to room temperature and stirring continued overnight. The solvent was removed under reduced pressure and the residue taken up in ether, washed with 1 molar aqueous hydrochloric acid, sodium bicarbonate solution and brine. The solution was dried, filtered and the solvent removed under reduced pressure to yield a yellow oil which was purified by chromatography using diethyl ether in petroleum ether (bp 60°-80°) as eluant to yield the subtitled compound (2.63 g, 92%).

1. customAfter a further 2 hours at room temperature the solvent was removed under reduced pressure
2. additionA further 50 ml of THF was added
3. temperaturethe mixture cooled to 0° at which point H2O2 (17 ml, 30% aqueous v/v)
4. additionwas added to the stirred solution over 1 hour
5. customThe solvent was removed under reduced pressure
6. washwashed with 1 molar aqueous hydrochloric acid, sodium bicarbonate solution and brine
7. customThe solution was dried
8. filtrationfiltered
9. customthe solvent removed under reduced pressure
10. customto yield a yellow oil which
11. customwas purified by chromatography

ORD record

ord-e16f9956e7f54821a41eb06781a97ec8

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05648370