Reacción #799100

Ecuación de reacción

1,8-octanediol

2,6-dinitrobenzonitrile

DBU

→

desired product

Rendimiento 62.3%

2-(8-hydroxyoctyloxy)-6-nitrobenzonitrile

Rendimiento 62.3%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe oily residue was triturated with 10% citric acid/water and solid NaCl
2. 2
   workup.ADDITIONadded
3. 3
   OtroThe precipitate was collected
4. 4
   Lavadowashed with water
5. 5
   Otrodried in vacuo
6. 6
   Otropurified on silica gel (40% to 100% EtOAc in hexanes)

Procedimiento

To a solution of 1,8-octanediol (3.87 mmol, 566 mg) in THF (dry, 10 mL) was added 2,6-dinitrobenzonitrile (1.29 mmol, 250 mg) and DBU (1.30 mmol, 194 μL). The reaction mixture was stirred for 24 hours at room temperature an evaporated. The oily residue was triturated with 10% citric acid/water and solid NaCl added. The precipitate was collected, washed with water, dried in vacuo and purified on silica gel (40% to 100% EtOAc in hexanes) to give the desired product (235 mg, 62.3%) as a pinkish solid. MS 293 (MH+).

Fuente