反応 #316270

反応方程式

sodium hydroxide

3-(6-Methoxy-7-oxiranylmethoxy-quinolin-4-yloxy)-5,6,5′-trimethyl-[2,2′]bipyridine

compound 457

3-(6-Methoxy-7-oxiranylmethoxy-quinolin-4-yloxy)-5,6,5′-trimethyl-[2,2′]bipyridine

Water

Trifluoroacetic acid

→

title compound

収率 63.0%

3-[6-Methoxy-4-(5,6,5′-trimethyl-[2,2′]bipyridin-3-yloxy)-quinolin-7-yloxy]-propane-1,2-diol

収率 63.0%

溶媒

methylene chloride

反応条件

後処理

1. 1
   その他to prepare a solution which
2. 2
   その他was then brought to 0° C
3. 3
   workup.WAITat room temperature for 5 hr
4. 4
   その他was brought to 0° C.
5. 5
   workup.STIRRINGwas stirred
6. 6
   抽出the mixture was extracted with chloroform
7. 7
   洗浄the chloroform layer was then washed with saturated brine
8. 8
   乾燥was dried over anhydrous sodium sulfate
9. 9
   その他The solvent was removed by distillation under the reduced pressure
10. 10
    その他the residue was purified by thin layer chromatography

実験手順

3-(6-Methoxy-7-oxiranylmethoxy-quinolin-4-yloxy)-5,6,5′-trimethyl-[2,2′]bipyridine (compound 457) (54 mg) was dissolved in methylene chloride (2 ml) to prepare a solution which was then brought to 0° C. Trifluoroacetic acid (1 ml) was added thereto, and the mixture was stirred at 0° C. for 30 min and then at room temperature for 5 hr. The reaction solution was brought to 0° C., was stirred and was made alkaline by the addition of a 10% aqueous sodium hydroxide solution. Water was added to the reaction solution, the mixture was extracted with chloroform, and the chloroform layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (35 mg, yield 63%).

出典