반응 #428351

반응 방정식

NaH

4-hydroxytetrahydropyran

4-bromo-2-chloropyridine

→

4-bromo-2-(tetrahydro-pyran-4-yloxy)-pyridine

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   기타before being quenched with EtOH (1 ml)
3. 3
   기타partitioned between CH2Cl2 and H2O
4. 4
   추출extracted CH2Cl2 (×2)
5. 5
   건조dried (MgSO4)
6. 6
   기타the solvent removed in vacuo
7. 7
   기타Purified by column chromatography

실험 절차

To a suspension of NaH (0.4 g, 10 mmol) in THF (20 ml) at 0° C. was added 4-hydroxytetrahydropyran (1.02 ml, 10 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 30 mins before 4-bromo-2-chloropyridine (0.89 ml, 8.0 mmol) was added dropwise. The reaction mixture was stirred for 18 h before being quenched with EtOH (1 ml), partitioned between CH2Cl2 and H2O and extracted CH2Cl2 (×2). The organics were combined, dried (MgSO4) and the solvent removed in vacuo. Purified by column chromatography to afford 4-bromo-2-(tetrahydro-pyran-4-yloxy)-pyridine MS: [MH]+ 258, 260

출처