Diethyl Ether → 1-Bromo-7-(prop-2-yn-1-yloxy)heptane

温度

60 °C

25% (w/w) aq. NaOH (700 ml) was added to a stirred mixture of propargyl alcohol (70 g), tetra-butyl ammonium bromide (3.5 g) and 1,7-dibromoheptane (322 g) maintaining the temperature below 30° C. The reaction mixture was heated at 60° C. for 5 hrs then allowed to cool to room temperature and stirred overnight. Diethyl ether (350 ml) and water (280 ml) were added, the mixture stirred and allowed to settle. The aqueous layer was extracted with diethyl ether (210 ml), the organic layers combined, dried (MgSO4). The solution was concentrated to give 280 g of crude material. 140 g Of the crude was purified by chromatography on Biotage (800 g) eluting with petroleum ether then petroleum ether:ethyl acetate (100:1 followed by 100:1.5) to give the title compound (49.6 g). NMR—300 MHz—δ (CDCl3)—4.05 (2H, d, J 2 Hz), 3.45 (2H, t, J 6.5 Hz), 3.35 (2H, t, J 7 Hz), 2.35 (1H, s), 1.8 (2H, m), 1.5 (2H, m), 1.3 (4H, m).

1. temperaturemaintaining the temperature below 30° C
2. temperatureto cool to room temperature
3. stirringthe mixture stirred
4. extractionThe aqueous layer was extracted with diethyl ether (210 ml)
5. dry with materialdried (MgSO4)
6. concentrationThe solution was concentrated
7. customto give 280 g of crude material
8. custom140 g Of the crude was purified by chromatography on Biotage (800 g)
9. washeluting with petroleum ether

ORDレコード

ord-928972620f544a12a2876e271dcbf73e

出典データセット

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07442719B2