Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-[4-hydroxy-3-(3-methoxypropoxy)phenyl]acrylate

HRID 1690607Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690607
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15].[CH2:16]([O:18][C:19]([CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:20])[CH3:17]>O1CCCC1>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:21][C:19]([O:18][CH2:16][CH3:17])=[O:20])=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15]

Komponenten

4

Edukt 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 866332964-Hydroxy-3-(3-methoxypropoxy)benzaldehyde

Produkt 1

HCID 66907011Ethyl 3-[4-hydroxy-3-(3-methoxypropoxy)phenyl]acrylateAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-hydroxy-3-(3-methoxypropoxy)benzaldehyde (15 g, 71.3 mmol) was dissolved in tetrahydrofuran (142 mL) and (ethoxycarbonylmethylene)triphenylphosphorane (24.8 g, 71.3 mmol) was added at room temperature portionwise. The mixture was then stirred overnight. The solvents were evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 8/2) to yield 16 g (80%) of the desired product as a yellow oil of a mixture of E and Z isomers.

Aufarbeitung

  1. customThe solvents were evaporated under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 8/2)
  3. customto yield

Quellen und Nachweise

ORD-Eintrag
ord-b9bb2d5107014abca499a34c8e4b323a
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153647B2

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