m-Formylbenzonitrile → 3-Ethenylbenzonitrile

HRID 898805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898805
[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]

Komponenten

5

Edukt 2

HCID 90670m-FormylbenzonitrileHCID 178418339Butyllithium

Produkt 1

HCID 2205433-EthenylbenzonitrileAusbeute 62,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-852856887a6847bb968bb81a98491c1a
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351822B2

Notizen zur Reaktion

Wird geladen…