تفاعل #11311

معادلة التفاعل

sodium bicarbonate

HCl

3-ethylenedioxy-1-phenylcyclohexanecarbonitrile

DIBAL-H

→

title compound

المردود 85.0%

3,3-ethylenedioxy-1-phenylcyclohexanecarbaldehyde

المردود 85.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGwas stirred for 1 hr
2. 2
   أخرىto quench
3. 3
   أخرىthe reaction
4. 4
   أخرىthe organic layer was separated
5. 5
   استخلاصThe aqueous layer was extracted with dichloromethane 3 times
6. 6
   تجفيفthe combined organic layers were dried over magnesium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated under vacuum
9. 9
   أخرىThe crude material was purified
10. 10
    ترشيحby filtering through a short silica gel pad with dichloromethane

الإجراء التجريبي

At −78° C., 3-ethylenedioxy-1-phenylcyclohexanecarbonitrile (1.66 g, 6.83 mmol) in toluene (20 mL) was added DIBAL-H (1.0 M solution in toluene, 8.88 mL) slowly and was stirred for 1 hr. The reaction mixture was warmed up to room temperature and was added 1N HCl solution (2.60 mL) and was stirred for 1 hr. Saturated sodium bicarbonate was added to quench the reaction 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 filtering through a short silica gel pad with dichloromethane to give the title compound as a white sticky oil (1.43 g, 85% yield). 1H NMR (400 MHz, CDCl3) δ 1.32–1.40 (1H, m), 1.46–1.54 (1H, m), 1.72–1.86 (3H, m), 2.08 (1H, d, J=16 Hz), 2.59–2.67 (2H, m), 3.94–4.07 (4H, m), 7.15–7.36 (5H, m), 9.36 (1H, d, J=4 Hz).

المصدر