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Dichloromethane → 5-(4'-Ethoxy-2,2',3,3'-tetrafluorobiphenyl-4-yl)-2-(4-propylcyclohexyl)tetrahydropyran

HRID 1941726
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1941726
ClCCl.[CH2:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:24][CH2:23][CH:22]([CH:25]4[CH2:30][CH2:29][CH:28]([CH2:31][CH2:32][CH3:33])[CH2:27][CH2:26]4)[O:21][CH:20]3O)=[C:15]([F:35])[C:14]=2[F:36])=[C:9]([F:37])[C:8]=1[F:38])[CH3:5].C([SiH](CC)CC)C>O>[CH2:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:20][O:21][CH:22]([CH:25]4[CH2:30][CH2:29][CH:28]([CH2:31][CH2:32][CH3:33])[CH2:27][CH2:26]4)[CH2:23][CH2:24]3)=[C:15]([F:35])[C:14]=2[F:36])=[C:9]([F:37])[C:8]=1[F:38])[CH3:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 12052TriethylsilaneHCID 585356523-(4'-Ethoxy-2,2',3,3'-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-ol

Produkt 1

HCID 585352905-(4'-Ethoxy-2,2',3,3'-tetrafluorobiphenyl-4-yl)-2-(4-propylcyclohexyl)tetrahydropyranAusbeute 36,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

Dichloromethane (30 ml) was added to 3-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-ol (12) (2.29 g) prepared in the tenth step. Triethylsilane (1.93 g) and a boron trifluoride-diethyl ether complex (2.37 g) were added dropwise to the solution at −30° C. After 3 hours of stirring, water (30 ml) was added to give two layers. The organic layer was washed with water, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 200 g, eluent: heptane/ethyl acetate=80/20 by volume) and then by recrystallization (heptane/ethyl acetate=90/10 by volume) to give 5-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)-2-(4-propylcyclohexyl)tetrahydropyran (13) (0.8 g) in 36% yield.

Aufarbeitung

  1. customprepared in the tenth step
  2. customto give two layers
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel chromatography (silica gel: 200 g, eluent: heptane/ethyl acetate=80/20 by volume)
  7. customby recrystallization (heptane/ethyl acetate=90/10 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-4e55451ca81348b89f47abdd944d3a5b
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08389073B2

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