2,6-Dimethyl-4-(hydroxymethyl)pyridine → 2,6-Dimethylpyridine-4-carbaldehyde

HRID 591819ノート

反応式

HRID 591819 の反応式
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([CH3:10])[CH:4]=1>CS(C)=O>[CH3:10][C:5]1[CH:4]=[C:3]([CH:2]=[O:1])[CH:8]=[C:7]([CH3:9])[N:6]=1

参加物

3

反応物 1

HCID 38250772,6-Dimethyl-4-(hydroxymethyl)pyridine

生成物 1

HCID 27630042,6-Dimethylpyridine-4-carbaldehyde

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

4-Hydroxymethyl-2,6-dimethylpyridine (24.7 g, 180 mmol, 1.0 equiv.) was dissolved in DMSO (200 mL), and IBX (53.0 g, 189 mmol, 1.05 equiv.) was added in portions, the mixture was stirred at room temperature for 2 hours; TLC indicated complete reaction. The mixture was filtered, washed with water and ether. The filtrate was extracted with ether (4×150 mL); the combined extracts were washed with water and brine, dried over anhydrous sodium sulfate, and concentrated to give the crude product, which was purified by column chromatography (20% ether in hexanes as eluent) to give 2,6-dimethyl-4-pyridinecarboxaldehyde as a yellow oil. Yield: 20.0 g (82%).

後処理

  1. additionIBX (53.0 g, 189 mmol, 1.05 equiv.) was added in portions
  2. customreaction
  3. filtrationThe mixture was filtered
  4. washwashed with water and ether
  5. extractionThe filtrate was extracted with ether (4×150 mL)
  6. washthe combined extracts were washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto give the crude product, which
  10. customwas purified by column chromatography (20% ether in hexanes as eluent)

出典と根拠

ORDレコード
ord-fa8a96c0e77243878b66d04ee82b668c
出典データセット
uspto-grants-2016_01
特許番号
US09238640B2

反応ノート

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