(2-Carboxyethyl)triphenylphosphonium chloride → (E)-4-(4-(1,4-Dihydro-4-oxo-1-pyridyl)phenyl)-3-butenoic acid

HRID 1647232

Reaktionsgleichung

[O:1]=[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)[CH:4]=[CH:3]1.[Cl-].[C:17]([CH2:20][CH2:21][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:19])=[O:18].CC(C)([O-])C.[K+]>O1CCCC1>[O:1]=[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:15]=[CH:14][C:11](/[CH:12]=[CH:21]/[CH2:20][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)[CH:4]=[CH:3]1

Komponenten

Reaktionsbedingungen

Temperatur: -5 °C

Versuchsvorschrift

4.0 g of 4-(1,4-dihydro-4-oxo-1-pyridyl)benzaldehyde and 8.2 g of β-carboxyethyltriphenylphosphonium chloride were suspended in 40 ml of tetrahydrofuran in a nitrogen atmosphere. The obtained suspension was cooled to -5° C., followed by the gradual addition of a solution of 4.96 g of potassium tertbutoxide in 30 ml of tetrahydrofuran. The temperature of the mixture was gradually raised to a room temperature. The resulting mixture was stirred for 14 hours, followed by the addition of ice-water. The obtained aqueous phase was washed with chloroform. The pH of the aqueous phase was adjusted with concentrated hydrochloric acid to about 3 to precipitate a crystal. This crystal was recovered by filtration and washed with water and methanol successively to obtain 3.48 g of the title compound as a pale yellow powder (yield: 68%).

Aufarbeitung

temperatureThe temperature of the mixture was gradually raised to a room temperature
washThe obtained aqueous phase was washed with chloroform
customto precipitate a crystal
filtrationThis crystal was recovered by filtration
washwashed with water and methanol successively

Quellen und Nachweise

ORD-Eintrag: ord-edb792883d4d409c8fa015a748d13684
Quelldatensatz: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05430059

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