Sodium borohydride → 1-(5-Bromopyridin-2-yl)ethanol

HRID 1501109ノート

反応式

HRID 1501109 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:10])[CH3:9])=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 231453451-(5-Bromopyridin-2-yl)ethan-1-one

生成物 1

HCID 426142881-(5-Bromopyridin-2-yl)ethanol収率 90%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 1-(5-bromopyridin-2-yl)ethanone (1.1 g, 5.5 mmol) in ethanol (100 mL) was added sodium borohydride (2.5 g, 66.1 mmol). The reaction mixture was stirred at room temperature for 24 hours. The mixture was filtered, the filtrate was acidified and the solvent removed on a rotary evaporator. The residue was taken up with water (50 mL) and extracted with dichloromethane (50 mL). The combined extract was dried over sodium sulfate, filtered, concentrated and purified by column chromatography to give 1-(5-bromopyridin-2-yl)ethanol (1.0 g, 90.0%) as a yellow oil. LRMS (M+H+) m/z: calcd 201.98. found 202. 1H NMR (300 MHz, CD3OD) δ 8.54 (d, J=2.4 Hz, 1H), 7.98 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 7.50 (d, J=8.4 Hz, 1H), 4.85 (m, 1H), 1.45 (d, J=6.6 Hz, 3H).

後処理

  1. filtrationThe mixture was filtered
  2. customthe solvent removed on a rotary evaporator
  3. extractionextracted with dichloromethane (50 mL)
  4. extractionThe combined extract
  5. dry with materialwas dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography

出典と根拠

ORDレコード
ord-8b24fbd6904b4b5787ece5fd6c5195c1
出典データセット
uspto-grants-2015_12
特許番号
US09206128B2

反応ノート

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