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A solution of 6-bromopyridin-3-ol (4.20 g) in N,N-dimethylformamide (100 mL) was purged with nitrogen, sodium hydride (60%, oil, 1.06 g) was added under ice-cooling, and the mixture was stirred at 0° C. for 15 min. Benzyl bromide (3.15 mL) was added to the reaction mixture, and the mixture was warmed to room temperature, and stirred at room temperature for 16 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-50:50, volume ratio) to give a colorless oil. A solution of the obtained oil in toluene (10 mL) was added to a solution of tributylmagnesium ate complex in toluene-tetrahydrofuran-hexane prepared from a 1.6M n-butyllithium hexane solution (8.4 mL) and a 2.0M butylmagnesium chloride tetrahydrofuran solution (3.4 mL) in at −10° C., and the mixture was stirred at −10° C. for 2.5 hr. N,N-dimethylformamide (1.59 mL) was added to the reaction mixture, and the mixture was warmed to room temperature and stirred at room temperature for 2 hr. 10% Aqueous citric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-50:50, volume ratio) to give the title compound (1.00 g, yield 17%) as a colorless oil. MS: 214 (MH+).

1. customA solution of 6-bromopyridin-3-ol (4.20 g) in N,N-dimethylformamide (100 mL) was purged with nitrogen, sodium hydride (60%, oil, 1.06 g)
2. additionwas added under ice-
3. temperaturecooling
4. additionBenzyl bromide (3.15 mL) was added to the reaction mixture
5. temperaturethe mixture was warmed to room temperature
6. stirringstirred at room temperature for 16 hr
7. additionA saturated aqueous ammonium chloride solution was added to the reaction mixture
8. extractionthe mixture was extracted with ethyl acetate
9. washThe extract was washed successively with water and saturated brine
10. dry with materialdried over anhydrous magnesium sulfate
11. concentrationconcentrated under reduced pressure
12. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-50:50, volume ratio)
13. customto give a colorless oil
14. temperaturethe mixture was warmed to room temperature
15. stirringstirred at room temperature for 2 hr
16. extractionthe mixture was extracted with ethyl acetate
17. washThe extract was washed successively with water and saturated brine
18. dry with materialdried over anhydrous magnesium sulfate
19. concentrationconcentrated under reduced pressure
20. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-50:50, volume ratio)