Benzyl Bromide → 5-(1-Benzyloxyethyl)-3-chloro-2-methylthiopyridine

3-Chloro-5-(1-hydroxyethyl)-2-methylthiopyridine (21.9 g, 0.108 mol) was dissolved with stirring in anhydrous DMF (250 mL) and 60% sodium hydride (5 g, 0.125 mol) added in portions. The mixture was stirred at room temperature for 30 minutes and benzyl bromide (17.6 g, 0.103 mol) added dropwise. The mixture was then stirred at room temperature for four hours, diluted with water (400 mL) and extracted three times with ethyl acetate (100 mL). The combined organic extracts were washed twice with water (200 mL) and saturated sodium chloride solution (100 mL), dried over anhydrous sodium sulphate, and evaporated to dryness. Purification of the residue by chromatography over silica (0-5% ethyl acetate:hexane) gave the desired product (25.0 g, 79%) as a pale yellow oil.

1. stirringThe mixture was then stirred at room temperature for four hours
2. extractionextracted three times with ethyl acetate (100 mL)
3. washThe combined organic extracts were washed twice with water (200 mL) and saturated sodium chloride solution (100 mL)
4. dry with materialdried over anhydrous sodium sulphate
5. customevaporated to dryness
6. customPurification of the residue by chromatography over silica (0-5% ethyl acetate:hexane)

ORD-Eintrag

ord-c20d86fecf30412aa22caa2368763ead

Quelldatensatz

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06306839B1