Sodium borohydride → (3-Bromopyridin-2-yl)methanol

HRID 423182

반응식

HRID 423182 반응식
C[O:2][C:3]([C:5]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][N:6]=1)=O.[BH4-].[Na+]>CO>[Br:11][C:10]1[C:5]([CH2:3][OH:2])=[N:6][CH:7]=[CH:8][CH:9]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 12828946Methyl 3-bromo-2-pyridinecarboxylate

생성물 1

HCID 14022521(3-Bromopyridin-2-yl)methanol수율 62%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

3-Bromo-pyridine-2-carboxylic acid methyl ester (12.8 g, 59.2 mmol) is dissolved in methanol (150 mL) and cooled to 0° C. To the mixture is added NaBH4 (11.2 g, 296 mmol) in 1.0 g portions. The mixture is warmed to room temperature and stirred for 3 h. The methanol is removed under reduced pressure, AcOEt is added and the solution is washed with saturated, aqueous ammonium chloride and brine. The organic portion is dried over MgSO4, filtered, and concentrated under reduced pressure to yield 6.8 g (62%) of the title compound as a white solid. GCMS m/e 187 [M−H]−.

후처리

  1. temperatureThe mixture is warmed to room temperature
  2. customThe methanol is removed under reduced pressure, AcOEt
  3. additionis added
  4. washthe solution is washed with saturated, aqueous ammonium chloride and brine
  5. dry with materialThe organic portion is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-90478131fd2643e281544e934bd8959d
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101761B2

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