تفاعل #56729

معادلة التفاعل

acetic acid

2,2,6-Trimethyl-heptanal

piperidine

benzyl cyanoacetate

HCl

→

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

المردود 61.6%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىThe flask was fitted with a Dean-Stark trap
2. 2
   درجة الحرارةthe mixture was heated
3. 3
   درجة الحرارةat reflux for 18
4. 4
   درجة الحرارةThe mixture was cooled
5. 5
   أخرىthe layers were separated
6. 6
   غسيلThe organics were washed with a saturated sodium bicarbonate solution
7. 7
   تجفيفdried (MgSO4)
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated
10. 10
    أخرىThe residual oil was purified by silica gel chromatography (98/2 hexane/EtOAc)

الإجراء التجريبي

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+).

المصدر