(Triphenylphosphoranylidene)acetaldehyde → (trans)-3-[3-(6-Phenyl-1,3,5-hexatriynyl)oxiranyl]-2-propenal

HRID 1906980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1906980
[C:1]1([C:7]#[C:8][C:9]#[C:10][C:11]#[C:12][C@@H:13]2[O:15][C@H:14]2[CH:16]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:18]([CH:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:19]>C1C=CC=CC=1>[C:1]1([C:7]#[C:8][C:9]#[C:10][C:11]#[C:12][C@@H:13]2[O:15][C@H:14]2[CH:16]=[CH:20][CH:18]=[O:19])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 86740799(trans)-3-(6-Phenyl-1,3,5-hexatriynyl)oxiranecarboxaldehyde

Produkt 1

HCID 86740800(trans)-3-[3-(6-Phenyl-1,3,5-hexatriynyl)oxiranyl]-2-propenalAusbeute 51,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

(trans)-3-(6-Phenyl-1,3,5-hexatriynyl)oxiranecarboxaldehyde (80 mg, 0.36 mmole; see example 4) and formylmethylenetriphenylphosphorane (122 mg, 0.40 mmole) were dissolved in 10 ml of dry benzene and the mixture was heated at 70° C. for 10 minutes. The mixture was then cooled to room temperature and the solvent was removed in vacuo. The residue was taken up in ether and filtered through a plug of silica gel. Removal of solvent afforded a brown oil which was purified by chromatography (silica gel, ether-hexane 1:1) to afford 46 mg of the title compound, melting point 91°-92.5° C.

Aufarbeitung

  1. temperatureThe mixture was then cooled to room temperature
  2. customthe solvent was removed in vacuo
  3. filtrationfiltered through a plug of silica gel
  4. customRemoval of solvent
  5. customafforded a brown oil which
  6. customwas purified by chromatography (silica gel, ether-hexane 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-978bacca33ea4b0c96525165a3d12246
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04654426

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