m-Formylbenzonitrile → 3-Ethenylbenzonitrile

HRID 1826595ノート

反応式

HRID 1826595 の反応式
[Li][CH2:2]CCC.[C:6]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)#[N:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:6]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[CH2:2])#[N:7]

参加物

5

反応物 2

HCID 90670m-FormylbenzonitrileHCID 178418339Butyllithium

生成物 1

HCID 2205433-Ethenylbenzonitrile収率 62.9%

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred suspension of methyltriphenylphosphonium bromide (75 g, 209.71 mmol) in dry THF (750 mL) at 0° C. under nitrogen was added dropwise n-BuLi (83 mL, 2.5 M in hexanes, 207.50 mmol). The mixture was warmed to room temperature. 3-Cyanobenzaldehyde (25 g, 190.65 mmol) was added as a solid in 5 g batches, and the mixture was stirred at room temperature overnight. The reaction was quenched in water, and the solvent was removed under vacuum. The residue was dissolved in the minimal amount of THF, and triphenylphosphine oxide was precipitated using ether. The solid was filtered through diatomaceous earth, and the filtrate was concentrated. Distillation by Kugelrhor at 90° C./33 Pa (0.25 mm Hg) gave the product as a colorless oil (15.5 g, 62%).

後処理

  1. customThe reaction was quenched in water
  2. customthe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in the minimal amount of THF, and triphenylphosphine oxide
  4. customwas precipitated
  5. filtrationThe solid was filtered through diatomaceous earth
  6. concentrationthe filtrate was concentrated
  7. distillationDistillation by Kugelrhor at 90° C./33 Pa (0.25 mm Hg)

出典と根拠

ORDレコード
ord-0a2510e73c644802b9286dd90eeea400
出典データセット
uspto-grants-2006_05
特許番号
US07053078B2

反応ノート

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