反応 #674308

反応方程式

EtOAc

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

p-toluenesulfonyl chloride

triethylamine

→

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

収率 36.0%

溶媒

DCM

反応条件

後処理

1. 1
   濃縮It was concentrated
2. 2
   その他to give the residue
3. 3
   洗浄The organic solution was washed with saturated NaHCO3 (30 mL), H2O (30 mL) and HCl (1.0 N, 30 mL), brine (30 mL)
4. 4
   乾燥dried over anhydrous Na2SO4
5. 5
   濃縮concentrated
6. 6
   その他to give yellow solid which
7. 7
   その他was purified by CombiFlash (24 g silica gel column, EtOAc/Hexane: 0-30%)

実験手順

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.

出典