Реакция #674308

Уравнение реакции

EtOAc

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

p-toluenesulfonyl chloride

triethylamine

→

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

Выход 36.0%

Растворители

DCM

Условия реакции

Обработка

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

Методика

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.

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