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

HRID 2175420Notes

Reaction equation

HRID 2175420 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

4

Reactant 3

HCID 6386tert-ButanolHCID 134006342-Ethynyl-5-methylpyridineHCID 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%).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for overnight
  3. customThe solvent was removed under reduced pressure
  4. customThe residue was purified by silca gel chromatography with the gradient eluent (PE/EA/NEt3=10/1/1%; 5/1/1%)

Sources & evidence

ORD record
ord-49e0f60196d24fdfae3616ed280245d7
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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