反应详情

4.2 g (145 mmol) of sodium hydride (80% in paraffin) are initially introduced in 100 ml of DMF with ice-cooling. 35.5 g (290 mmol) of 1,4-butanedithiol are slowly added dropwise. After the evolution of gas has ended, 15.3 g (97 mmol) of 4-chloro-2-hydroxymethyl-3-methylpyridine in 20 ml of DMF are added drop-wise. After about 30 minutes, the mixture is allowed to come to RT and is stirred at this temperature for 12 h. It is diluted with 800 ml of ice-water and neutralized with acetic acid. The mixture is extracted 3 times with dichloromethane. The combined organic phases are washed 4 times with water, dried over magnesium sulfate, filtered and concentrated. The crude product is chromatographed on silica gel using ethyl acetate/conc. ammonia=99/1. The title compound is obtained as a yellow crystallizate. M.p. 58°-63° C.; yield 13 g (55% of theory).

1. temperaturecooling
2. customto come to RT
3. extractionThe mixture is extracted 3 times with dichloromethane
4. washThe combined organic phases are washed 4 times with water
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product is chromatographed on silica gel