Reaktion #590186

Reaktionsgleichung

2-[5-(2-chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]-2-methylpropanal

Benzyltriphenylphosphonium bromide

n-butyllithium

→

3-(2-chlorophenyl)-5-[(2E)-1,1-dimethyl-3-phenylprop-2-en-1-yl]-4-methyl-1,2,4-triazol

Ausbeute 10.6%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe whole was stirred
2. 2
   Temperaturunder heating
3. 3
   Temperaturrefluxing for 20 hours
4. 4
   SonstigeThe reaction mixture was quenched with water (50 ml)
5. 5
   Extraktionextracted with ethyl acetate (50 ml×2)
6. 6
   WaschenThe organic layer washed with a 1M aqueous hydrochloric acid solution (30 ml)
7. 7
   SonstigeThe organic layer was dried
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   Sonstigethe resulting residue was purified by silica gel column chromatography (methanol:chloroform=2:98) and preparative thin layer chromatography (ethyl acetate:hexane=3:1)

Vorschrift

Benzyltriphenylphosphonium bromide (1.15 g) was suspended in THF (30 ml) and, under ice cooling, n-butyllithium (1.60M hexane solution, 1.50 ml) was added thereto, followed by stirring at room temperature for 30 minutes. A THF (20 ml) solution of 2-[5-(2-chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]-2-methylpropanal (633 mg) was added dropwise to the reaction solution and the whole was stirred under heating and refluxing for 20 hours. The reaction mixture was quenched with water (50 ml) and then extracted with ethyl acetate (50 ml×2). The organic layer washed with a 1M aqueous hydrochloric acid solution (30 ml), a saturated aqueous sodium bicarbonate solution, and a brine (30 ml). The organic layer was dried and then concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (methanol:chloroform=2:98) and preparative thin layer chromatography (ethyl acetate:hexane=3:1) to obtain 86 mg of 3-(2-chlorophenyl)-5-[(2E)-1,1-dimethyl-3-phenylprop-2-en-1-yl]-4-methyl-1,2,4-triazol (white solid).

Quelle