Sodium Chloride → 5-(3-Chloropropoxy)-2-pyridine methanol

To the stirred solution of 32.32 g of 5-hydroxy-2-pyridinemethanol hydrochloride in 200 ml of dimethylformamide is added 18.2 g of sodium hydride (50% mineral oil dispersion) in portions while maintaining a temperature of 50°-55° of the mixture. Then the mixture is stirred at 50°-55° for 30 minutes and then is added a solution of 31.5 g of 1-bromo-3-chloropropane in 50 ml of dimethylformamide, while maintaining a temperature below 50° of the mixture. After that, the mixture is allowed to come to room temperature and is additionally stirred at room temperature for 2 hours and 30 minutes. Then the mixture is poured into 1,200 ml of water, the aqueous mixture is saturated with sodium chloride and the resulting saturated solution extracted three times with ether. The ether extracts are combined, the combined ether solution is washed and dried over anhydrous magnesium sulfate. The ether solution is filtered and the filtrate evaporated to yield 5-(3-chloropropoxy)-2 -pyridinemethanol.

1. temperaturewhile maintaining a temperature of 50°-55° of the mixture
2. temperaturewhile maintaining a temperature below 50° of the mixture
3. customto come to room temperature
4. stirringis additionally stirred at room temperature for 2 hours and 30 minutes
5. extractionthe resulting saturated solution extracted three times with ether
6. washthe combined ether solution is washed
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationThe ether solution is filtered
9. customthe filtrate evaporated

ORD record

ord-129b34d0c8c5452590650d6dfdb1dedc

Source dataset

uspto-grants-1981_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04260620