Reacción #9899

Ecuación de reacción

NBS

6-cyclobutyl-hexan-1-ol

triphenylphosphine

→

(6-bromo-hexyl)-cyclobutane

Rendimiento 91.3%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction was quenched with methanol (0.5 mL)
2. 2
   workup.ADDITIONThe solution was diluted with ether (60 mL)
3. 3
   Lavadowashed with water, saturated aqueous NaHCO3 and brine successively
4. 4
   OtroThe organic layer was dried
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe residue was purified by flash chromatography on silica gel
7. 7
   Lavadoeluting with hexane

Procedimiento

To a solution of 6-cyclobutyl-hexan-1-ol (0.47 g, 3.0 mmol) in DMF (10 mL) was added triphenylphosphine (0.88 g, 3.4 mmol). The solution was cooled to 0° C. and NBS (0.57 g, 3.2 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.5 mL). The solution was diluted with ether (60 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 (6-bromo-hexyl)-cyclobutane (0.60 g, 91%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.40 (2H, t, J=6.9 Hz), 2.23 (1H, m), 2.02 (2H, m), 1.82 (4H, m), 1.55 (2H, m), 1.12–1.46 (8H, m); 13C NMR (75 MHz, CDCl3) δ 37.19, 36.39, 34.40, 33.11, 29.07, 28.68, 28.51, 27.26, 18.80.

Fuente