تفاعل #9886

معادلة التفاعل

NBS

cis-oct-3-en-1-ol

triphenylphosphine

→

cis-1-bromo-oct-3-ene

المردود 91.1%

المذيبات

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر