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Ammonia → HCID 178466082, Verbindung

HRID 2088249
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2088249
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]3)=[C:18]([F:29])[C:17]=2[F:30])=[C:12]([F:31])[C:11]=1[F:32])[CH3:8].C(OCC)(=O)C.N>C1COCC1>[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C@H:22]3[CH2:23][CH2:24][C@H:25]([OH:28])[CH2:26][CH2:27]3)=[C:18]([F:29])[C:17]=2[F:30])=[C:12]([F:31])[C:11]=1[F:32])[CH3:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 58453654HCID 58453654, Verbindung

Produkt 1

HCID 178466082HCID 178466082, VerbindungAusbeute 240,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

Lithium aluminum hydride (0.31 g) was suspended in THF (100 ml). 1-(4′-Ethoxy-2,2′,3,3′-tetrafluoro-1,1′-biphenyl-4-yl)-cyclohexan-4-one (s-27) (5.0 g) dissolved in THF (20 ml) was added dropwide to the suspension in the temperature range of −20° C. to −10° C., and the stirring was continued in this temperature range for another 2 hours. After the completion of the reaction had been confirmed by means of GC analysis, ethyl acetate and then a saturated aqueous solution of ammonia were added to the reaction mixture under ice-cooling and deposits were removed by filtration through Celite. The filtrate was extracted with ethyl acetate. The combined organic phase was washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by recrystallization from heptane to give trans-4-(4′-ethoxy-2,2′,3,3′-tetrafluoro-1,1′-biphenyl-4-yl)-cyclohexanol (s-28) (12.1 g). The yield based on the compound (s-27) was 89.1%.

Aufarbeitung

  1. additionwas added dropwide to the suspension in the temperature range of −20° C. to −10° C.
  2. temperaturecooling
  3. customdeposits were removed by filtration through Celite
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washThe combined organic phase was washed successively with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by recrystallization from heptane

Quellen und Nachweise

ORD-Eintrag
ord-cf04f5bfe9d54fc29f6ce4fec2ef328f
Quelldatensatz
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08435422B2

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