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

HRID 1909548

Reaktionsgleichung

Reaktionsgleichung von HRID 1909548
[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-fbe773790a124d9987d1933f8f5716e3
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598374B2

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