Reacción #412433

Ecuación de reacción

methyl phenyl sulfone

HCl

nBuLi

diisopropylamine

1-bromo-2-cyclohexylethane

→

oil

Rendimiento 52.0%

3-Cyclohexylpropyl phenyl sulfone

Rendimiento 52.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe cold bath was removed
2. 2
   Temperaturato warm to ambient temperature
3. 3
   workup.STIRRINGstir for 18 hours
4. 4
   Extracciónfollowed by extraction with EtOAc (2×)
5. 5
   Secadodried (MgSO4)
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue was chromatographed (silica gel; EtOAc/hexanes, 1:8)

Procedimiento

A solution of 2.5M nBuLi in hexanes (1.9 mL, 4.7 mmol) was added to a solution of diisopropylamine (660 μL, 4.7 mmol) in THF (9.0 mL) at ambient temperature. After 10 min, the mixture was cooled to −78° C. and methyl phenyl sulfone (700 mg, 4.5 mmol) was added to the reaction vessel. The cold bath was removed and after stirring for 30 min, 1-bromo-2-cyclohexylethane (1.3 g, 6.7 mmol) was added to the reaction mixture. The mixture was allowed to warm to ambient temperature and stir for 18 hours. A solution of 2N HCl was added to the reaction mixture followed by extraction with EtOAc (2×). The organic phases were combined, dried (MgSO4) and concentrated. The residue was chromatographed (silica gel; EtOAc/hexanes, 1:8) to afford a clear oil (620 mg, 52%). 1H NMR (CDCl3, MHz) δ 0.75-0.91 (m, 2H), 1.07-1.26 (m, 6H), 1.58-1.76 (m, 7H), 3.06 (t, J=8 Hz, 2H), 7.55-7.70 (m, 3H), 7.92 (m, 2H); MS (CI/NH3) m/z: (M+NH4)+ 284.

Fuente