Ethyl 5-(2-phenyleth-1-ynyl)nicotinate → (E)-(5-Styrylpyridin-3-yl)-methanol

참여 물질

반응 단계

Add a solution of commercially available 5-phenylethynyl-nicotinic acid ethyl ester (0.4 g, 1.59 mmol) in dry tetrahydrofuran (20 mL) to a solution of lithium aluminum hydride (20 mL, 0.08 M in tetrahydrofuran) at room temperature under nitrogen and stir for 3 h. Add a solution of lithium aluminum hydride (2 mL, 1 M in tetrahydrofuran) and stir for 1 h. Slowly add methanol (2 mL) and concentrate. Dilute with ethyl acetate, wash with water and a saturated aqueous solution of sodium chloride and dry. Purify the residue by silica gel chromatography, eluting with 5:1 hexanes:ethyl acetate to 10:90 hexanes:ethyl acetate, to give the E-isomer (7 mg, 2%).

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