反応 #473057

反応方程式

Sodium hydride

Tetrahydro-2H-thiopyran-4-ol

2-Bromo-6-(bromomethyl)pyridine

→

title compound

2-Bromo-6-[(tetrahydro-2H-thiopyran-4-yloxy)methyl]pyridine

溶媒

tetrahydrofuran

ethyl acetate

反応条件

後処理

1. 1
   温度the reaction was warmed to and
2. 2
   温度maintained at ambient temperature overnight
3. 3
   その他quenched slowly with water
4. 4
   その他the layers were separated
5. 5
   抽出the aqueous layer was extracted with ethyl acetate
6. 6
   乾燥The combined organic layers were dried over magnesium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated
9. 9
   その他The crude mixture was purified by silica gel chromatography

実験手順

Sodium hydride (0.24 g, 5.98 mmol) was suspended in tetrahydrofuran (19.9 mL) and cooled to 0° C. Tetrahydro-2H-thiopyran-4-ol (0.24 g, 1.99 mmol) was added and the reaction was stirred for 30 minutes. 2-Bromo-6-(bromomethyl)pyridine (Example 190, Step 1) (0.5 g, 1.99 mmol) was added and the reaction was warmed to and maintained at ambient temperature overnight. The reaction was diluted with ethyl acetate, quenched slowly with water, the layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated. The crude mixture was purified by silica gel chromatography to yield the title compound.

出典