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Ammonium Chloride → 1-(2,3-Difluoro-4-(4-pentylcyclohexyl)phenyl)-4-(4-ethoxy-2,3-difluorophenyl)cyclohexanol

HRID 1943559
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1943559
[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=2[F:19])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C([Li])(CC)C.[CH2:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([CH:34]2[CH2:39][CH2:38][C:37](=[O:40])[CH2:36][CH2:35]2)=[C:30]([F:41])[C:29]=1[F:42])[CH3:26].[Cl-].[NH4+]>C1COCC1.C1(C)C=CC=CC=1.C1CCCCC1.CCCCCC>[F:18][C:14]1[C:13]([F:19])=[C:12]([CH:9]2[CH2:10][CH2:11][CH:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8]2)[CH:17]=[CH:16][C:15]=1[C:37]1([OH:40])[CH2:36][CH2:35][CH:34]([C:31]2[CH:32]=[CH:33][C:28]([O:27][CH2:25][CH3:26])=[C:29]([F:42])[C:30]=2[F:41])[CH2:39][CH2:38]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 25517Ammonium ChlorideHCID 111611214-(4-Ethoxy-2,3-difluorophenyl)cyclohexanoneHCID 199109694-Pentyl-(2,3-difluorophenyl)cyclohexaneHCID 178418400CID 53628100

Produkt 1

HCID 670824391-(2,3-Difluoro-4-(4-pentylcyclohexyl)phenyl)-4-(4-ethoxy-2,3-difluorophenyl)cyclohexanolAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 8078CyclohexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-Pentyl-(2,3-difluorophenyl)cyclohexane (10) (5.0 g) and THF (100 ml) were put in a reaction vessel under a nitrogen atmosphere, and cooled to −74° C. sec-Butyllithium (1.00 M, in a n-hexane and cyclohexane solution; 23.0 ml) was added dropwise thereto in the temperature range of −74° C. to −70° C., and the mixture was stirred for another 2 hours. 1-(4-Ethoxy-2,3-difluorophenyl)-cyclohexan-4-one (50) (4.8 g) dissolved in THF (150 ml) was slowly added dropwise thereto in the temperature range of −74° C. to −70° C., and the stirring was continued for another 8 hours while the mixture was allowed to return to 25° C. The reaction mixture obtained was poured into a vessel containing an aqueous solution of ammonium chloride (3%; 500 ml) and toluene (300 ml) which had been cooled to 0° C., and mixed. The mixture was then allowed to stand until it had separated into organic and aqueous phases, and extraction into an organic phase was carried out. The organic phase obtained was fractionated, washed sequentially with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, giving 9.7 g of 1-(2,3-difluoro-4-(4-pentylcyclohexyl)phenyl)-4-(4-ethoxy-2,3-difluorophenyl)cyclohexanol (51). The compound (51) obtained was a yellow solid.

Aufarbeitung

  1. addition23.0 ml) was added dropwise
  2. additionwas slowly added dropwise
  3. waitin the temperature range of −74° C. to −70° C., and the stirring was continued for another 8 hours while the mixture
  4. customto return to 25° C
  5. customThe reaction mixture obtained
  6. additionwas poured into a vessel
  7. additionmixed
  8. customhad separated into organic and
  9. extractionaqueous phases, and extraction into an organic phase
  10. customThe organic phase obtained
  11. washwashed sequentially with water
  12. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate
  13. distillationThen, the solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e3328f74e1f2473eb92ca05d62dd96fa
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08394294B2

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