反応 #1347363

反応方程式

4-iodotetrahydropyran

trans-2-aminocyclohexanol hydrochloride

sodium hexamethyldisilazide

4-cyanophenylboronic acid

→

title compound

4-(Tetrahydro-2H-pyran-4-yl)benzonitrile

溶媒

isopropanol

反応条件

後処理

1. 1
   その他The suspension thus obtained
2. 2
   workup.STIRRINGAfter the reaction mixture had been stirred at a temperature of 75° C. for 15 h
3. 3
   温度it was cooled to RT
4. 4
   ろ過substantially freed of inorganic salts with dichloromethane by filtration through approx. 50 g of silica gel
5. 5
   その他The crude product was purified by MPLC (silica gel, eluent: dichloromethane)

実験手順

186 mg (0.594 mmol) of nickel(II) iodide, 90 mg (0.594 mmol) of trans-2-aminocyclohexanol hydrochloride and 3.63 g (19.8 mmol) of sodium hexamethyldisilazide were added to a solution of 2.91 g (19.8 mmol) of 4-cyanophenylboronic acid [M. Nishimura et al., Tetrahedron 2002, 58 (29), 5779-5788] in 20 ml of isopropanol. The suspension thus obtained was stirred at RT under an argon atmosphere for 5 min. Then 2.1 g (9.90 mmol) of 4-iodotetrahydropyran [Heuberger et al., J. Chem. Soc. 1952, 910] were added. After the reaction mixture had been stirred at a temperature of 75° C. for 15 h, it was cooled to RT and substantially freed of inorganic salts with dichloromethane by filtration through approx. 50 g of silica gel. The crude product was purified by MPLC (silica gel, eluent: dichloromethane). 986 mg (53% of theory) of the title compound were obtained.

出典