Reaktion #674308

Reaktionsgleichung

EtOAc

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

p-toluenesulfonyl chloride

triethylamine

→

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

Ausbeute 36.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle