tert-Butanol → (Z)-2-(2-tert-butoxyvinyl)-5-methylpyridine
反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][N:4]=1)#[CH:2].[C:10]([OH:14])([CH3:13])([CH3:12])[CH3:11].CC(C)([O-])C.[K+]>>[C:10]([O:14]/[CH:2]=[CH:1]\[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][N:4]=1)([CH3:13])([CH3:12])[CH3:11]参加物
4
実験手順
To the solution of 2-ethynyl-5-methylpyridine (12-2) (1.38 g, 11.8 mmol) in tert-butyl alcohol (4.734 g, 63.9 mmol) was added potassium tert-butoxide (531 mg, 4.7 mmol) under nitrogen. The solution was heated to reflux for overnight. The solvent was removed under reduced pressure. The residue was purified by silca gel chromatography with the gradient eluent (PE/EA/NEt3=10/1/1%; 5/1/1%). The product (Z)-2-(2-tert-butoxyvinyl)-5-methylpyridine (12-3) was obtained as yellow oil (1.40 g, 62%) and by product was (E)-2-(2-tert-butoxyvinyl)-5-methylpyridine (0.3 g, 13%).