(2-(Dimethylamino)ethyl)triphenylphosphonium bromide → (E)-3-{6-[3-Dimethylamino-1-(4-tolyl)prop-1E-enyl]-2-pyridyl}acrylic acid

HRID 542503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 542503
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([C:7]([C:9]2[N:14]=[C:13](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])[CH:12]=[CH:11][CH:10]=2)=O)=[CH:3][CH:2]=1.[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])C=CC=CC=1>>[CH3:32][N:31]([CH3:33])[CH2:30]/[CH:29]=[C:7](/[C:9]1[N:14]=[C:13](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])[CH:12]=[CH:11][CH:10]=1)\[C:4]1[CH:5]=[CH:6][C:1]([CH3:20])=[CH:2][CH:3]=1

Komponenten

3

Edukt 2

HCID 2724136(2-(Dimethylamino)ethyl)triphenylphosphonium bromideHCID 11971260(E)-3-[6-(p-toluoyl)-2-pyridyl]acrylic acid

Produkt 1

HCID 13191753(E)-3-{6-[3-Dimethylamino-1-(4-tolyl)prop-1E-enyl]-2-pyridyl}acrylic acid

Versuchsvorschrift

Treatment of (E)-3-[6-(4-toluoyl)-2-pyridyl]acrylic acid, vide supra, with the Wittig reagent derived from triphenyldimethylaminoethylphosphonium bromide by the method of example 1 gave a mixture of isomeric acids which were separated by fractional crystallization from ethyl acetate. The less-soluble E-isomer, (E)-3-{6-[3-dimethylamino-1-(4-tolyl)prop-1E-enyl]-2-pyridyl}acrylic acid was puried by crystallization from isopropanol, m.p. 222°-225° (decomp.)

Aufarbeitung

  1. customgave
  2. additiona mixture of isomeric acids which
  3. customwere separated by fractional crystallization from ethyl acetate
  4. customThe less-soluble E-isomer, (E)-3-{6-[3-dimethylamino-1-(4-tolyl)prop-1E-enyl]-2-pyridyl}acrylic acid was puried by crystallization from isopropanol, m.p. 222°-225° (decomp.)

Quellen und Nachweise

ORD-Eintrag
ord-bb30646c33b748e8bfa63b5d63a33c6b
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04657918

Notizen zur Reaktion

Wird geladen…