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

HRID 593583노트

반응식

HRID 593583 반응식
[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

참가 물질

5

반응물 3

HCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 45051731Sodium hexamethyidisilazaneHCID 178503020HCID 178503020, 화합물

생성물 1

HCID 234363373-Bromo-5-vinylpyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-d75969a0a89e484e81f163570b97c08b
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242963B2

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