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Hydrochloric Acid → 2-(Propenyl)-5-[4-(4-propylcyclohexyl)phenyl]selenophene

HRID 1873389
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1873389
[CH3:1][C:2](C)([O-])C.[K+].[CH2:7]([CH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[Se:26][C:25]([CH:27]=O)=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)[CH2:8][CH3:9].Cl>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1COCC1.CC(OC)(C)C.[Cl-].[NH4+]>[CH:27]([C:25]1[Se:26][C:22]([C:19]2[CH:20]=[CH:21][C:16]([CH:13]3[CH2:14][CH2:15][CH:10]([CH2:7][CH2:8][CH3:9])[CH2:11][CH2:12]3)=[CH:17][CH:18]=2)=[CH:23][CH:24]=1)=[CH:1][CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 594562815-[4-(4-Propylcyclohexyl)phenyl]selenophene-2-carbaldehyde

Produkt 1

HCID 722902572-(Propenyl)-5-[4-(4-propylcyclohexyl)phenyl]selenophene

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Katalysator
HCID 8028TetrahydrofuranLösungsmittel2×
HCID 15413tert-Butyl methyl etherLösungsmittel
HCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

1.80 g (4.85 mmol) of ethyltriphenylphosphonium bromide are initially introduced in 8 ml of THF at 0° C., and 533 mg (4.75 mmol) of potassium tert-butoxide are added. After 1.5 h at RT, a solution of 1.16 g (3.23 mmol) of 5-[4-(4-propylcyclohexyl)phenyl]selenophene-2-carbaldehyde in 7 ml of THF is added, and the batch is stirred for 2.5 h. The mixture is diluted with MTBE, and sat. ammonium chloride soln. and 2 N hydrochloric acid are added. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride soln. and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane→n-heptane:EtOAc=20:1). 2-(Propenyl)-5-[4-(4-propylcyclohexyl)phenyl]selenophene is obtained as an E/Z isomer mixture.

Aufarbeitung

  1. customThe organic phase is separated off
  2. extractionthe aqueous phase is extracted with MTBE
  3. washThe combined organic phases are washed with sat. sodium chloride soln
  4. customand dried
  5. concentrationThe solution is concentrated to dryness
  6. customthe residue is purified by column chromatography (SiO2, n-heptane→n-heptane:EtOAc=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-d5bb2c20a2c24e3886367c461b81c583
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08304036B2

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