反应 #159258

反应方程式

ammonium chloride

5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one

6-Bromo-2-naphthoic acid

n-butyllithium

→

title compound

收率 12.2%

6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-2-naphthoic acid

收率 12.2%

溶剂

ethyl acetate

THF

THF

hexane

反应条件

后处理

1. 1
   workup.ADDITIONwas added dropwise at −95° C. or below over 5 min
2. 2
   温度the mixture was cooled to −100° C. again
3. 3
   workup.STIRRINGAfter stirring at the same temperature for 30 min
4. 4
   温度the temperature was raised to −70° C. over 30 min
5. 5
   其他to quench
6. 6
   其他the reaction
7. 7
   workup.STIRRINGAfter stirring for 10 min
8. 8
   其他to partition the solution
9. 9
   其他The organic layer was removed
10. 10
    浓缩the aqueous layer was concentrated to dryness
11. 11
    其他The obtained residue was purified by flash column chromatography
12. 12
    workup.DISSOLUTIONthe object fraction was dissolved in methanol
13. 13
    浓缩This solution was concentrated
14. 14
    workup.ADDITIONether was added to the precipitated powder
15. 15
    过滤the powder was collected by filtration
16. 16
    其他dried

实验过程

6-Bromo-2-naphthoic acid (1.51 g) was dissolved in dry THF (50 ml), and cooled to −100° C. in a liquid nitrogen/diethyl ether bath. Under stirring a solution (1.6M; 7.88 ml) of n-butyllithium in hexane was added dropwise at −95° C. or below over 5 min. After stirring at −100° C. for 30 min and at −80° C. for 10 min, the mixture was cooled to −100° C. again. A solution of 5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one (0.61 g) in dry THF (11 ml) was added dropwise at −90° C. or below over 5 min. After stirring at the same temperature for 30 min, the temperature was raised to −70° C. over 30 min, and saturated aqueous ammonium chloride solution (25 ml) was added to quench the reaction. After stirring for 10 min, ethyl acetate (50 ml) was added to partition the solution. The organic layer was removed and the aqueous layer was concentrated to dryness. The obtained residue was purified by flash column chromatography, and the object fraction was dissolved in methanol. This solution was concentrated, ether was added to the precipitated powder and the powder was collected by filtration and dried. The title compound (180 mg) was obtained as a colorless powder. The mother liquor was concentrated to give a residue (449 mg) containing the title compound.

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