Reaction #6235

Reaction equation

4-hydroxypyridine

N-(4bromobutyl)phthalimide

1,8-diazabicyclo[5.4.0]-7-undecene

→

desired compound

Yield 17.8%

4-(4-phthalimidobutyloxy)pyridine

Yield 17.8%

Solvents

DMF

Conditions

Workup

1. 1
   workup.DISTILLATIONAfter the solvent was distilled off
2. 2
   workup.ADDITIONthe mixture was poured into water
3. 3
   Extractionextracted with ethyl acetate
4. 4
   WashThe mixture was washed with water
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off
7. 7
   OtherThe residue was purified by column chromatography (eluent: ethyl acetate)

Procedure

To a solution of 4.76 g (50 mmol) of 4-hydroxypyridine and 15.52 g (55 mmol) of N-(4bromobutyl)phthalimide in 80 ml of DMF was added 8.23 ml (5 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene. The mixture was stirred at room temperature for 7 hours. After the solvent was distilled off, the mixture was poured into water and extracted with ethyl acetate. The mixture was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 2.63 g of the desired compound (yield: 17.2%, colorless crystals).

Source