반응 #558963

반응 방정식

1,8-octanediol

2,6-dinitrobenzonitrile

DBU

→

desired product

수율 62.3%

2-(8-hydroxyoctyloxy)-6-nitrobenzonitrile

수율 62.3%

용매

THF

반응 조건

후처리

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

실험 절차

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+).

출처