5-Bromo-3-pyridinecarboxaldehyde → 3-Bromo-5-vinylpyridine

HRID 1630853ノート

反応式

HRID 1630853 の反応式
[Br-].[CH3:2]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si](C)(C)N[Si](C)(C)C.[Na].[Br:32][C:33]1[CH:34]=[C:35]([CH:39]=O)[CH:36]=[N:37][CH:38]=1>O1CCCC1>[Br:32][C:33]1[CH:38]=[N:37][CH:36]=[C:35]([CH:39]=[CH2:2])[CH:34]=1

参加物

5

反応物 3

HCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 45051731Sodium hexamethyidisilazaneHCID 178503020HCID 178503020、化合物

生成物 1

HCID 234363373-Bromo-5-vinylpyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyltriphenylphosphine bromide (3.16 g, 8.87 mmol) in tetrahydrofuran (20 mL) is added sodium hexamethyldisilazane (1M solution in THF, 9.67 mL, 9.67 mmol) dropwise. The reaction mixture is stirred at room temperature for 30 min, whereupon 5-bromo-pyridine-3-carbaldehyde (1.5 g, 8.06 mmol) is added. The reaction mixture is allowed to stir at room temperature for 1 h. The mixture is concentrated and the residue is purified by silica gel flash chromatography (heptane-ethyl acetate, 7:3) to afford 3-bromo-5-vinyl-pyridine as a colorless oil. MS (ESI) m/z 185.91 (M+H)+.

後処理

  1. additionis added
  2. concentrationThe mixture is concentrated
  3. customthe residue is purified by silica gel flash chromatography (heptane-ethyl acetate, 7:3)

出典と根拠

ORDレコード
ord-b567c1da8ed945aab02601c67cdeec7a
出典データセット
uspto-grants-2014_07
特許番号
US08791141B2

反応ノート

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