تفاعل #156513

معادلة التفاعل

5-fluoro-2-methylbenzaldehyde

nitroethane

cyclohexylamine

→

designed compound

المردود 89.0%

4-Fluoro-1-methyl-2-(2-nitroprop-1-enyl)benzene

المردود 89.0%

المذيبات

acetic acid

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was cooled to rt
2. 2
   أخرىthe solvent was removed under vacuum
3. 3
   workup.ADDITIONThe residue was diluted with water
4. 4
   استخلاصextracted with ethyl acetate three times
5. 5
   تجفيفThe combined extracts were dried over anhydrous MgSO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated under vacuum
8. 8
   أخرىProduct was purified by a silica gel chromatography

الإجراء التجريبي

A mixture of 5-fluoro-2-methylbenzaldehyde (50.0 g, 0.382 mol), nitroethane (54.34 g, 0.724 mol), and cyclohexylamine (35.90 g, 0.382 mol) in 300 mL of acetic acid was heated at 80° C. for 5-6 h under an argon atmosphere. After the end of the reaction was established by TLC, the reaction mixture was cooled to rt and the solvent was removed under vacuum. The residue was diluted with water, extracted with ethyl acetate three times. The combined extracts were dried over anhydrous MgSO4, filtered, and concentrated under vacuum. Product was purified by a silica gel chromatography using ethyl acetate and hexanes (1:6 to 1:4) as eluent to afford 62.8 g (89%) of the designed compound as yellow solid. Mass (ESI, positive) m/z 217.9 [M+Na]+.

المصدر