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Cesium fluoride → 4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-[(1Z)-1-propenyl]-6-propylphenol

HRID 1919758
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1919758
[F-].[Cs+].[CH:3](/B(O)O)=[CH:4]/[CH3:5].[F:9][C:10]([F:32])([F:31])[C:11]([C:20]1[CH:25]=[C:24]([CH2:26][CH2:27][CH3:28])[C:23]([OH:29])=[C:22](I)[CH:21]=1)([O:16][CH2:17][O:18][CH3:19])[C:12]([F:15])([F:14])[F:13]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:9][C:10]([F:32])([F:31])[C:11]([C:20]1[CH:25]=[C:24]([CH2:26][CH2:27][CH3:28])[C:23]([OH:29])=[C:22](/[CH:3]=[CH:4]\[CH3:5])[CH:21]=1)([O:16][CH2:17][O:18][CH3:19])[C:12]([F:15])([F:14])[F:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 25953Cesium fluorideHCID 5355539(Z)-Prop-1-en-1-ylboronic acidHCID 59234900HCID 59234900, Verbindung

Produkt 1

HCID 592350754-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-[(1Z)-1-propenyl]-6-propylphenolAusbeute 181,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Cesium fluoride (1.24 g), cis-propenylboronic acid (1.54 g) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.49 g) were added to a mixed solution of 4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-iodo-6-propylphenol (2.83 g, 5.99 mmol) in toluene (60 mL) in an argon atmosphere at room temperature, followed by stirring overnight. After completion of the reaction, the reaction solution was extracted with ethyl acetate-water, and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 4.20 g of the title compound (yield: 85%) as a brown solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionthe reaction solution was extracted with ethyl acetate-water
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-777abd5c36164d63940b4d099d1284f3
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08168666B2

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