Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → 3-(2-Ethoxycarbonylethenyl)-2-methyl-7-nitrobenzo[b]furan

HRID 342433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342433
[CH:1]([C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=2[O:6][C:7]=1[CH3:8])=O.[C:16]([CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:18][CH2:19][CH3:20])=[O:17]>O1CCOCC1>[CH2:19]([O:18][C:16]([CH:21]=[CH:1][C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=2[O:6][C:7]=1[CH3:8])=[O:17])[CH3:20]

Komponenten

4

Edukt 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 867535523-Formyl-2-methyl-7-nitrobenzo[b]furan

Produkt 1

HCID 702015513-(2-Ethoxycarbonylethenyl)-2-methyl-7-nitrobenzo[b]furanAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 3-formyl-2-methyl-7-nitrobenzo[b]furan (200 mg) and (carboethoxymethylene)triphenylphosphorane (434 mg) in dioxane (3 ml) was stirred at ambient temperature for 1 hour. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel. The obtained oil was crystallized from diisopropyl ether to give 3-(2-ethoxycarbonylethenyl)-2-methyl-7-nitrobenzo[b]furan (226 mg).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography on silica gel
  3. customThe obtained oil was crystallized from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ef9c129ac1434376ae4f1fb958ae3d48
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05858995

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