Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-(5-(benzyloxy)-2-methylphenyl)acrylate

HRID 709689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 709689
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:17])=[C:13]([CH:16]=1)[CH:14]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:17])=[C:13]([CH:14]=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 600256215-(Benzyloxy)-2-methylbenzaldehyde

Produkt 1

HCID 131733902Ethyl 3-(5-(benzyloxy)-2-methylphenyl)acrylateAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 5-(benzyloxy)-2-methylbenzaldehyde (250 mg) in toluene (20 mL) was added ethyl (triphenylphosphoranylidene)acetate (379 mg), and the mixture was stirred at 60° C. for 15 hr. The reaction mixture was concentrated, diethyl ether was added, and the insoluble material was filtered off. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (200 mg) as a yellow oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additiondiethyl ether was added
  3. filtrationthe insoluble material was filtered off
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c4fa1aea91e7475e9198735ac107cb04
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181186B2

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