Water → 6-Bromohexylbut-3-ynyl ether

3-Butyn-1-ol (42.4 ml) was stirred vigorously with 1,6-dibromohexane (260 ml) and tetrabutylammonium bisulphate (2.4 g) in 50% aqueous sodium hydroxide solution (200 ml) under nitrogen for 3 days. Water (ca 700 ml) was added and the organic layer was separated. The aqueous layer was extracted twice with dichloromethane (2×100 ml) and the combined organic layers were washed with water, dried (MgSO4) and concentrated. The residue in petroleum ether (bp 40–60°) was loaded onto a column of silica gel (1.5 kg) and the column was eluted with petroleum ether (bp 40–60°), then 10% diethyl ether in petroleum ether (bp 40–60°) to give the title compound (103.3 g), δ (CDCl3) 3.56(2H, t, J 7 Hz), 3.47(2H, t, J 7 Hz), 3.42(2H, t, J 7 Hz), 2.45(2H, m), 1.99(1H, t, J 2 Hz), 1.87(2H, m), 1.60(2H, m) and 1.50 to 1.33 (4H, m).

1. customthe organic layer was separated
2. extractionThe aqueous layer was extracted twice with dichloromethane (2×100 ml)
3. washthe combined organic layers were washed with water
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. washthe column was eluted with petroleum ether (bp 40–60°)

ORD record

ord-6c06e00836f54613a734bcf9869aea17

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07135600B2