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

HRID 423182

反応式

HRID 423182 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 14022521(3-Bromopyridin-2-yl)methanol収率 62%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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]−.

後処理

  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

出典と根拠

ORDレコード
ord-90478131fd2643e281544e934bd8959d
出典データセット
uspto-grants-2012_01
特許番号
US08101761B2

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