반응 #421656

반응 방정식

5-bromonicotinaldehyde

NaBH4

→

(5-bromopyridin-3-yl)methanol

수율 90.0%

용매

MeOH

반응 조건

후처리

1. 1
   농축The mixture was concentrated in vacuo
2. 2
   workup.ADDITIONthe residue was diluted in water (15 mL)
3. 3
   추출the aqueous phase was extracted with DCM (10 mL×3)
4. 4
   건조The combined organic layers were dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo

실험 절차

To a solution of 5-bromonicotinaldehyde (XLVII) (2.0 g, 10.8 mmol, 1 eq) in MeOH (20 mL) was added NaBH4 (2.4 g, 64.9 mmol, 6 eq) and the reaction mixture was stirred at room temperature for 3 h. The mixture was concentrated in vacuo and the residue was diluted in water (15 mL), the aqueous phase was extracted with DCM (10 mL×3). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to afford (5-bromopyridin-3-yl)methanol (LVI) (1.8 g, 9.57 mmol, 90.0% yield) as a colorless oil. 1H NMR (CDCl3, 500 MHz) δ ppm 4.73 (s, 2H), 7.90 (s, 1H), 8.47 (s, 1H), 8.57 (s, 1H). ESIMS found for C6H6BrNO m/z 188 (M+H).

출처