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Water → 6-(3-Acetylaminophenyl)-6-(3-pyridyl)hex-5-enoic acid

HRID 374825
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 374825
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].CC(C)([O-])C.[K+].C(NC1C=C([C:44]2[C:49]([C:50]([C:52]3[C:53]([C:58]4C=CC=[C:60]([NH:64][C:65](=[O:67])[CH3:66])[CH:59]=4)=NC=C[CH:57]=3)=O)=[CH:48][CH:47]=[CH:46][N:45]=2)C=CC=1)(=O)C.O>O1CCCC1>[C:65]([NH:64][C:60]1[CH:57]=[C:52]([C:50]([C:49]2[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=2)=[CH:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])[CH:53]=[CH:58][CH:59]=1)(=[O:67])[CH3:66]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 53837382HCID 53837382, Verbindung

Produkt 1

HCID 537920006-(3-Acetylaminophenyl)-6-(3-pyridyl)hex-5-enoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a mixture of 217 g of 4-carboxybutyl-triphenylphosphonium bromide and 154 g of potassium tert.butoxide in 1.8 liters of tetrahydrofuran are added, at -25° C., 94 g of 3-acetylaminophenyl-3-pyridyl ketone. After 2 hours stirring at ambient temperature the reaction mixture is combined with 200 ml of water and then substantially evaporated down. The residue is taken up in 500 ml of water and washed with ethyl acetate. The aqueous phase is then neutralised by the addition of citric acid and extracted with ethyl acetate. The organic phase is evaporated down and the residue is recrystallised from ethyl acetate/acetone.

Aufarbeitung

  1. additionare added, at -25° C.
  2. customsubstantially evaporated down
  3. washwashed with ethyl acetate
  4. additionThe aqueous phase is then neutralised by the addition of citric acid
  5. extractionextracted with ethyl acetate
  6. customThe organic phase is evaporated down
  7. customthe residue is recrystallised from ethyl acetate/acetone

Quellen und Nachweise

ORD-Eintrag
ord-0bc1f5315ad34ca48e606dd262ce8542
Quelldatensatz
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05482948

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