반응 #56729

반응 방정식

acetic acid

2,2,6-Trimethyl-heptanal

piperidine

benzyl cyanoacetate

HCl

→

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

수율 61.6%

용매

toluene

반응 조건

후처리

1. 1
   기타The flask was fitted with a Dean-Stark trap
2. 2
   온도the mixture was heated
3. 3
   온도at reflux for 18
4. 4
   온도The mixture was cooled
5. 5
   기타the layers were separated
6. 6
   세척The organics were washed with a saturated sodium bicarbonate solution
7. 7
   건조dried (MgSO4)
8. 8
   여과filtered
9. 9
   농축concentrated
10. 10
    기타The residual oil was purified by silica gel chromatography (98/2 hexane/EtOAc)

실험 절차

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+).

출처