반응 #2495502

반응 방정식

3-aminobenzaldehyde ethylene acetal

4-bromodibenzo[b,d]thiophene

Sodium tert-butoxide

tri-tert-butylphosphine

→

N-(3-(1,3-dioxolan-2-yl)phenyl)dibenzo[b,d]thiophen-4-amine

용매

toluene

toluene

반응 조건

후처리

1. 1
   기타A clean and dry 1000 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
5. 5
   기타The reaction solution was purged with a strong nitrogen flow for 20 minutes
6. 6
   온도The vessel was heated
7. 7
   온도to reflux for approximately 2 hours
8. 8
   여과filtered through a Celite and silica gel pad
9. 9
   기타Solvent was removed by rotary evaporation
10. 10
    workup.DISSOLUTIONThe crude material was dissolved in a 2:1 hexane/ethyl acetate solution
11. 11
    기타purified by flash column chromatography

실험 절차

A clean and dry 1000 ml round bottom flask equipped with a reflux condenser, magnetic stir bar, and thermometer with adapter was prepared and purged with nitrogen. A solution of 4-bromodibenzo[b,d]thiophene (RS-1-170, 10.7 g, 0.0407 mol) in anhydrous toluene (500.0 ml) was then prepared and transferred to the reaction flask via cannula. 3-aminobenzaldehyde ethylene acetal (8.1 g, 0.0488 mol) was added by syringe. The reaction solution was purged with a strong nitrogen flow for 20 minutes. Sodium tert-butoxide (5.86 g, 0.0610 mol) and Pd2dba3 (1.10 g, 0.0012 mol) were then added manually, followed by the addition of tri-tert-butylphosphine (0.65 g, 0.0032 mol) in toluene (−10 ml) via syringe. The vessel was heated to reflux for approximately 2 hours. The reaction was then cooled to room temperature and filtered through a Celite and silica gel pad. Solvent was removed by rotary evaporation. The crude material was dissolved in a 2:1 hexane/ethyl acetate solution purified by flash column chromatography using a gradient elution system of ethyl acetate/hexane. This provided pure product confirmed by NMR.

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