Toluene → (E)-ethyl 3-(5-hydroxy-[1,1'-biphenyl]-2-yl)acrylate

HRID 445833

Reaktionsgleichung

Reaktionsgleichung von HRID 445833
[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([CH:14]=O)=[CH:4][CH:3]=1.[C:16]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:18])=[O:17].[C:39]1(C)C=CC=C[CH:40]=1>>[OH:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:14]=[CH:19]/[C:16]([O:18][CH2:39][CH3:40])=[O:17])=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=1

Komponenten

4

Edukt 3

HCID 1140TolueneHCID 10870911Carboxymethylene triphenylphosphoraneHCID 573034645-Hydroxy-[1,1'-biphenyl]-2-carbaldehyde

Produkt 1

HCID 58566652(E)-ethyl 3-(5-hydroxy-[1,1'-biphenyl]-2-yl)acrylate

Versuchsvorschrift

A solution of 5-hydroxy-[1,1′-biphenyl]-2-carbaldehyde (651) (292 mg, 1.47 mmol) and (carboxymethylene)-triphenylphosphorane (564.5 mg, 1.62 mmol) in toluene (15 mL) was refluxed for 24 hours. The reaction was concentrated in vacuo and was purified by flash column chromatography on silica gel with hexanes and EtOAc (30%) to give (E)-ethyl 3-(5-hydroxy-[1,1′-biphenyl]-2-yl)acrylate (652).

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. customwas purified by flash column chromatography on silica gel with hexanes and EtOAc (30%)

Quellen und Nachweise

ORD-Eintrag
ord-b776ab79d0c74eb6beb4ac9bf981ef7f
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476308B2

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