Reaktion #54355

Reaktionsgleichung

3-[4-(1,1-dimethylheptyl)-2-allyloxyphenyl]-1-N-(2-propenyl)-1,2,5,6-tetrahydropyridine

3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-1,2,5,6-tetrahydropyridine

potassium carbonate

allyl bromide

→

title compound

Ausbeute 22.0%

3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1-N-(2-propenyl)-1,2,5,6-tetrahydropyridine

Ausbeute 22.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA mixture of 1.0 g
2. 2
   Temperaturat reflux for 23 hours
3. 3
   EinengenThe reaction mixture is concentrated under reduced pressure
4. 4
   workup.DISSOLUTIONthe residue dissolved in 250 ml
5. 5
   ExtraktionThe organic extract
6. 6
   Waschenis washed once with 100 ml
7. 7
   Trocknenof saturated sodium chloride, dried over magnesium sulfate
8. 8
   Sonstigeevaporated to an oil
9. 9
   SonstigeThe oil is purified via column chromatography on 125 g
10. 10
    Waschenof silica gel eluted with 5% methanol-dichloromethane
11. 11
    Sonstigeto yield 372 mg

Vorschrift

A mixture of 1.0 g. (3.32 mmoles) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-1,2,5,6-tetrahydropyridine, 539 mg. (3.90 mmoles) of anhydrous potassium carbonate and 401 mg. (3.32 mmoles) of allyl bromide in 23 ml. of ethanol is heated at reflux for 23 hours. The reaction mixture is concentrated under reduced pressure and the residue dissolved in 250 ml. of saturated sodium bicarbonate and 200 ml. of dichloromethane. The organic extract is washed once with 100 ml. of saturated sodium chloride, dried over magnesium sulfate and evaporated to an oil. The oil is purified via column chromatography on 125 g. of silica gel eluted with 5% methanol-dichloromethane to yield 372 mg. (29%) of 3-[4-(1,1-dimethylheptyl)-2-allyloxyphenyl]-1-N-(2-propenyl)-1,2,5,6-tetrahydropyridine as an oil and 247 mg. (22%) of the title compound, M.P. 109°-110° C. (from ether-pentane). Title Compound: PMR: αCDCl3TMS 0.85 (m, terminal methyl), 1.25 (s, gem dimethyl), 3.23 (m, allyl methylene), 5.0-5.4 and 5.5-6.1 (m, four vinyl protons), 6.82 (m, ArH) and 6.97 (d, J=8Hz, ArH).

Quelle