تفاعل #70673

معادلة التفاعل

2-(3-bromophenyl)-1,3-dioxolane

1-naphthylamine

Sodium tert-butoxide

tri-tert-butylphosphine

→

N-(3-(1,3-dioxolan-2-yl)phenyl)naphthalen-1-amine

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىA clean and dry 500 ml round bottom flask
2. 2
   أخرىequipped with a reflux condenser, magnetic stir bar
3. 3
   أخرىthermometer with adapter was prepared
4. 4
   أخرىpurged with nitrogen Anhydrous toluene (250.0 ml)
5. 5
   أخرىwas transferred to this flask by cannula
6. 6
   أخرىThe reaction solution was purged with a strong nitrogen flow for 30 minutes
7. 7
   درجة الحرارةThe vessel was heated
8. 8
   درجة الحرارةto reflux for approximately 5 hours
9. 9
   ترشيحfiltered through a Celite and silica gel pad
10. 10
    غسيلwashing thoroughly with acetone and chloroform
11. 11
    أخرىSolvent was removed by rotary evaporation
12. 12
    أخرىThe crude material was purified by flash column chromatography

الإجراء التجريبي

A clean and dry 500 ml round bottom flask equipped with a reflux condenser, magnetic stir bar, and thermometer with adapter was prepared and purged with nitrogen Anhydrous toluene (250.0 ml) was transferred to this flask by cannula. 2-(3-bromophenyl)-1,3-dioxolane (6.0 ml, 0.0397 mol) was added by syringe followed by the manual addition of 1-naphthylamine (5.08 g, 0.0355 mol). The reaction solution was purged with a strong nitrogen flow for 30 minutes. Sodium tert-butoxide (5.60 g, 0.0583 mol) and Pd2dba3 (0.65 g, 0.0007 mol) were then added manually, followed by the addition of tri-tert-butylphosphine (1.30 g, 0.0064 mol) in toluene (˜10 ml) via syringe. The vessel was heated to reflux for approximately 5 hours. The reaction was then cooled to room temperature and filtered through a Celite and silica gel pad washing thoroughly with acetone and chloroform. Solvent was removed by rotary evaporation. The crude material was purified by flash column chromatography using ethyl acetate/hexane as an eluent. This provided pure product confirmed by NMR spectroscopy.

المصدر