Reacción #674308

Ecuación de reacción

EtOAc

4-(benzyloxy)-1-(hydroxymethyl)cyclohexanecarbonitrile

p-toluenesulfonyl chloride

triethylamine

→

(4-(benzyloxy)-1-cyanocyclohexyl)methyl 4-methylbenzenesulfonate

Rendimiento 36.0%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónIt was concentrated
2. 2
   Otroto give the residue
3. 3
   LavadoThe organic solution was washed with saturated NaHCO3 (30 mL), H2O (30 mL) and HCl (1.0 N, 30 mL), brine (30 mL)
4. 4
   Secadodried over anhydrous Na2SO4
5. 5
   Concentraciónconcentrated
6. 6
   Otroto give yellow solid which
7. 7
   Otrowas purified by CombiFlash (24 g silica gel column, EtOAc/Hexane: 0-30%)

Procedimiento

To a solution of 4-(benzyloxy)-1-(hydroxymethyl)cyclohexanecarbonitrile (crude 770 mg, 1.0 equiv) in DCM (7 mL) was added p-toluenesulfonyl chloride (898 mg, 1.5 equiv), triethylamine (1.44 mL, 3.3 equiv) and DMAP (38 mg, 0.1 equiv). The solution was stirred at room temperature overnight. It was concentrated to give the residue. EtOAc (120 mL) was added. The organic solution was washed with saturated NaHCO3 (30 mL), H2O (30 mL) and HCl (1.0 N, 30 mL), brine (30 mL), dried over anhydrous Na2SO4 and then concentrated to give yellow solid which was purified by CombiFlash (24 g silica gel column, EtOAc/Hexane: 0-30%) to afford 450 mg (yield 36%) of (4-(benzyloxy)-1-cyanocyclohexyl)methyl 4-methylbenzenesulfonate as a white solid.

Fuente