tert-Butanol → (Z)-2-(2-tert-butoxyvinyl)-5-methylpyridine

Reaction equation

[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]

Participants

Reactant 3

HCID 6386tert-Butanol

HCID 134006342-Ethynyl-5-methylpyridine

HCID 23665647Potassium tert-butoxide

Product 1

HCID 86729575(Z)-2-(2-tert-butoxyvinyl)-5-methylpyridine

Procedure

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%).