Hydrochloric Acid → 2-(4'-Ethyl-3-fluorobiphenyl-4-yl)-5-propenylthiophene

HRID 1943516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943516
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:19][C:18]([CH:20]=O)=[CH:17][CH:16]=3)=[C:11]([F:22])[CH:10]=2)=[CH:5][CH:4]=1)[CH3:2].[CH3:23][C:24](C)([O-])C.[K+].O.Cl>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1COCC1>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:19][C:18]([CH:20]=[CH:23][CH3:24])=[CH:17][CH:16]=3)=[C:11]([F:22])[CH:10]=2)=[CH:5][CH:4]=1)[CH3:2]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 581606825-(4'-Ethyl-3-fluorobiphenyl-4-yl)thiophene-2-carbaldehyde

Produkt 1

HCID 670675042-(4'-Ethyl-3-fluorobiphenyl-4-yl)-5-propenylthiophene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)KatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

26.0 g (70.0 mmol) of ethyltriphenylphosphonium bromide are initially introduced in 400 ml of THF together with 20.0 g (62.6 mmol) of 5-(4′-ethyl-3-fluorobiphenyl-4-yl)thiophene-2-carbaldehyde, and a solution of 7.86 g (70.0 mmol) of potassium tert-butoxide in 100 ml of THF is added with ice-cooling. The mixture is stirred at room temperature for 20 h. Water and 2 N hydrochloric acid are added, and the batch is extracted with MTBE. The organic phase is washed with sat. sodium chloride solution and dried using sodium sulfate. The solution is evaporated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane:toluene 9:1→toluene).

Aufarbeitung

  1. temperaturecooling
  2. extractionthe batch is extracted with MTBE
  3. washThe organic phase is washed with sat. sodium chloride solution
  4. customdried
  5. customThe solution is evaporated to dryness
  6. customthe residue is purified by column chromatography (SiO2, n-heptane:toluene 9:1→toluene)

Quellen und Nachweise

ORD-Eintrag
ord-62267da294d043da953d384abbb06a52
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394293B2

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