Reaktion #56729

Reaktionsgleichung

acetic acid

2,2,6-Trimethyl-heptanal

piperidine

benzyl cyanoacetate

HCl

→

2-Cyano-4,4,8-trimethyl-non-2-enoic acid benzyl ester

Ausbeute 61.6%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe flask was fitted with a Dean-Stark trap
2. 2
   Temperaturthe mixture was heated
3. 3
   Temperaturat reflux for 18
4. 4
   TemperaturThe mixture was cooled
5. 5
   Sonstigethe layers were separated
6. 6
   WaschenThe organics were washed with a saturated sodium bicarbonate solution
7. 7
   Trocknendried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe residual oil was purified by silica gel chromatography (98/2 hexane/EtOAc)

Vorschrift

To a mixture of 2,2,6-Trimethyl-heptanal (1.05 g, 6.73 mmol), piperidine (0.19 mL, 2.01 mmol) and benzyl cyanoacetate (1.29 g, 7.4 mmol) in toluene (50 mL) was added glacial acetic acid (0.72 g, 12.1 mmol). The flask was fitted with a Dean-Stark trap, and the mixture was heated at reflux for 18. The mixture was cooled, treated with dilute HCl, and the layers were separated. The organics were washed with a saturated sodium bicarbonate solution followed by brine, and dried (MgSO4), filtered and concentrated. The residual oil was purified by silica gel chromatography (98/2 hexane/EtOAc) to give 1.3 g of 2-Cyano-4,4,8-trimethyl-non-2-enoic acid benzyl ester m/z 314 (M+).

Quelle