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

HRID 709707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 709707
[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=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[C:10]([CH3:17])=[C:11]([CH:12]=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:14]=[CH:15][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 159481993-(Benzyloxy)-2-methylbenzaldehyde

Produkt 1

HCID 131733904Ethyl 3-(3-(benzyloxy)-2-methylphenyl)acrylateAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 3-(benzyloxy)-2-methylbenzaldehyde (200 mg) in toluene (20 mL) was added ethyl (triphenylphosphoranylidene)acetate (303 mg), and the mixture was stirred at 60° C. for 15 hr. The reaction mixture was concentrated, and diethyl ether was added. The insoluble material was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (120 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-15f250e1f8084f8082ed0495004dea02
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181186B2

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