반응 #9886

반응 방정식

NBS

cis-oct-3-en-1-ol

triphenylphosphine

→

cis-1-bromo-oct-3-ene

수율 91.1%

용매

DMF

반응 조건

후처리

1. 1
   기타the reaction was quenched with methanol (1 mL)
2. 2
   workup.ADDITIONThe solution was diluted with ether (100 mL)
3. 3
   세척washed with water, saturated aqueous NaHCO3 and brine successively
4. 4
   기타The organic layer was dried
5. 5
   농축concentrated
6. 6
   기타The residue was purified by flash chromatography on silica gel
7. 7
   세척eluting with hexane

실험 절차

To a solution of cis-oct-3-en-1-ol (1.00 g, 7.81 mmol) in DMF (18 mL) was added triphenylphosphine (2.28 g, 8.69 mmol). The solution was cooled to 0° C. and NBS (1.50 g, 8.43 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution was diluted with ether (100 mL), washed with water, saturated aqueous NaHCO3 and brine successively. The organic layer was dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexane to afford cis-1-bromo-oct-3-ene (1.36 g, 91%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.53 (1H, m), 5.35 (1H, m), 3.36 (2H, t, J=7.2 Hz), 2.60 (2H, m), 2.04 (2H, m), 1.33 (4H, m), 0.89 (3H, t, J=7.2 Hz); 3C NMR (75 MHz, CDCl3) δ 133.27, 125.84, 32.93, 31.97, 31.12, 27.43, 22.64, 14.30.

출처