تفاعل #78761

معادلة التفاعل

KF

N-methylpyrrole

TMEDA

n-BuLi

3-bromo-benzaldehyde

Me3SnCl

→

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

المردود 40.5%

المذيبات

ethyl acetate

Et2O

dioxane

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe solution was heated
2. 2
   درجة الحرارةto reflux under N2 for 1 h
3. 3
   درجة الحرارةAfter warming to room temperature
4. 4
   درجة الحرارةThe slurry was heated
5. 5
   درجة الحرارةto reflux for 18 h
6. 6
   workup.STIRRINGstirred 15 min
7. 7
   ترشيحThe slurry was filtered through celite
8. 8
   أخرىThe organic layer was separated
9. 9
   غسيلwashed with brine
10. 10
    تجفيفdried (MgSO4)
11. 11
    أخرىevaporated to an oil
12. 12
    أخرىPurification by flash chromatography on silica gel eluting with 5% ethyl acetate in hexane

الإجراء التجريبي

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]+.

المصدر