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

HRID 593583ノート

反応式

HRID 593583 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-d75969a0a89e484e81f163570b97c08b
出典データセット
uspto-grants-2016_01
特許番号
US09242963B2

反応ノート

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