1-Hexanol → 5-Bromo-2-hexyloxypyridine

Temperature

80 °C

A solution of 300 mmol of 1-hexanol in 100 ml of DMF is added dropwise at 50° C. under a protective gas to a suspension of 300 mmol of sodium hydride (80 percent in mineral oil) in 100 ml of dry DMF. The mixture is stirred at 80° C. for 1 hour, and a solution of 200 mmol of 2,5-dibromopyridine in 150 ml of warm DMF is subsequently slowly added dropwise. The mixture is then stirred at 80° C. for 3-4 hours. For hydrolysis, the cooled reaction mixture is introduced into 1 l of ice/water, the mixture is extracted a number of times with dichloromethane, and the combined organic extracts are washed with sat. sodium chloride solution and dried using sodium sulfate. After the solvent has been removed in vacuo, the residue is chromatographed on silica gel 60 using dichloromethane as eluent, giving 52 g (quant. yield) of a viscous liquid.

1. stirringThe mixture is then stirred at 80° C. for 3-4 hours
2. customFor hydrolysis
3. customthe cooled reaction mixture
4. extractionthe mixture is extracted a number of times with dichloromethane
5. washthe combined organic extracts are washed with sat. sodium chloride solution
6. customdried
7. customAfter the solvent has been removed in vacuo
8. customthe residue is chromatographed on silica gel 60 using dichloromethane as eluent

ORD record

ord-a0fdd0cd01bb4e1fbdac1dd9d4e7776b

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06022492