تفاعل #674308

معادلة التفاعل

EtOAc

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

p-toluenesulfonyl chloride

triethylamine

→

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

المردود 36.0%

المذيبات

DCM

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر