반응 #70673

반응 방정식

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

용매

toluene

반응 조건

후처리

1. 1
   기타A clean and dry 500 ml round bottom flask
2. 2
   기타equipped with a reflux condenser, magnetic stir bar
3. 3
   기타thermometer with adapter was prepared
4. 4
   기타purged with nitrogen Anhydrous toluene (250.0 ml)
5. 5
   기타was transferred to this flask by cannula
6. 6
   기타The reaction solution was purged with a strong nitrogen flow for 30 minutes
7. 7
   온도The vessel was heated
8. 8
   온도to reflux for approximately 5 hours
9. 9
   여과filtered through a Celite and silica gel pad
10. 10
    세척washing thoroughly with acetone and chloroform
11. 11
    기타Solvent was removed by rotary evaporation
12. 12
    기타The crude material was purified by flash column chromatography

실험 절차

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.

출처