تفاعل #11310

معادلة التفاعل

3-oxo-1-phenylcyclohexanecarbonitrile

ethylene glycol

pyridinium p-toluene sulfonate

→

title compound

المردود 48.0%

3,3-ethylenedioxy-1-phenylcyclohexanecarbonitrile

المردود 48.0%

المذيبات

benzene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling down to room temperature
2. 2
   غسيلthe mixture was washed with saturated sodium bicarbonate
3. 3
   أخرىthe organic layer was separated
4. 4
   استخلاصThe aqueous layer was extracted with dichloromethane 3 times
5. 5
   تجفيفthe combined organic layers were dried over magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated under vacuum
8. 8
   أخرىThe crude material was purified by Flash Chromatography with from 25% ethyl acetate/75% hexane to 30% ethyl acetate/70% hexane over 20 minutes

الإجراء التجريبي

The mixture of 3-oxo-1-phenylcyclohexanecarbonitrile (2.62 g), ethylene glycol (3.65 mL) and pyridinium p-toluene sulfonate (1 spatula) in benzene (40 mL) was stirred at 111° C. with Dean-Stark apparatus overnight. After cooling down to room temperature, the mixture was washed with saturated sodium bicarbonate and the organic layer was separated. The aqueous layer was extracted with dichloromethane 3 times and the combined organic layers were dried over magnesium sulfate, filtered and concentrated under vacuum. The crude material was purified by Flash Chromatography with from 25% ethyl acetate/75% hexane to 30% ethyl acetate/70% hexane over 20 minutes. The title compound was obtained as a white solid (1.66 g, 48% yield in 2 steps). 1H NMR (400 MHz, CDCl3) δ 1.56 (1H, dt, J=4, 16 Hz), 1.70–1.79 (1H, m), 1.89–1.96 (3H, m), 2.06–2.28 (3H, m), 3.89–3.97 (2H, m), 4.03–4.12 (2H, m), 7.28–7.32 (1H, m), 7.36–7.39 (2H, m), 7.48–7.51 (2H, m). HPLC purity (retention time): 95% (1.62 min, method C). MS: 266.37 (M+Na+).

المصدر