反应详情

To a solution of methyl 4-pyridylacetate (Step A, 2.5 g, 16 mmol) and benzyl alcohol (3.4 mL, 33 mmol) in anhydrous tetrahydrofuran (10 mL) at −10° C. was added butyllithium (2 M in cyclohexane, 16 mL, 33 mL), and the reaction was allowed to warm to room temperature overnight. The volatile materials were removed on a rotary evaporator, and the residue was diluted with methylene chloride (50 mL), washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to dryness, and the residue was purified by flash column chromatography eluted with 30% ethyl acetate in hexane to give the title compound. 1H NMR (400 MHz, CD3OD): δ 8.43 (d, 2H), 7.38 (d, 2H), 7.32 (m, 5 H), 5.16 (s, 2H), 3.99 (s, 2H).

1. customThe volatile materials were removed on a rotary evaporator
2. additionthe residue was diluted with methylene chloride (50 mL)
3. washwashed with water and brine
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated to dryness
7. customthe residue was purified by flash column chromatography
8. washeluted with 30% ethyl acetate in hexane