반응 #78761

반응 방정식

KF

N-methylpyrrole

TMEDA

n-BuLi

3-bromo-benzaldehyde

Me3SnCl

→

3-(1-methyl-1H-pyrrol-2-yl)benzaldehyde

수율 40.5%

용매

ethyl acetate

Et2O

dioxane

THF

반응 조건

후처리

1. 1
   온도The solution was heated
2. 2
   온도to reflux under N2 for 1 h
3. 3
   온도After warming to room temperature
4. 4
   온도The slurry was heated
5. 5
   온도to reflux for 18 h
6. 6
   workup.STIRRINGstirred 15 min
7. 7
   여과The slurry was filtered through celite
8. 8
   기타The organic layer was separated
9. 9
   세척washed with brine
10. 10
    건조dried (MgSO4)
11. 11
    기타evaporated to an oil
12. 12
    기타Purification by flash chromatography on silica gel eluting with 5% ethyl acetate in hexane

실험 절차

EX-602A) To solution of N-methylpyrrole (0.97 mL, 11 mmol) in Et2O (20 mL) was added neat TMEDA (1.5 mL, 10 mmol) and 1.6 M n-BuLi in hexanes (6.3 mL, 10 mmol). The solution was heated to reflux under N2 for 1 h and then cooled to −78° C. A 1.0 M solution of Me3SnCl in THF was added over 15 min, and the resulting solution stirred for 30 min at −78° C. After warming to room temperature, 3-bromo-benzaldehyde (0.70 mL, 6.0 mmol), Pd(PPh3)2Cl2 (0.25 g, 0.35 mmol) and dioxane (10 mL) were added. The slurry was heated to reflux for 18 h. The cooled mixture was poured into a mixture of saturated KF and ethyl acetate and stirred 15 min. The slurry was filtered through celite. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated to an oil. Purification by flash chromatography on silica gel eluting with 5% ethyl acetate in hexane gave 0.45 g (24%) of the desired 3-(1-methyl-1H-pyrrol-2-yl)benzaldehyde product as a yellow oil. MS: m/z=186.2 [M+H]+.

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