Toluene → 3-(4'-Ethoxy-2,2',3,3'-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-ol

HRID 1941725Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1941725
C1(C)C=CC=CC=1.[CH2:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]3[CH2:28][CH2:27][CH:26]([CH:29]4[CH2:34][CH2:33][CH:32]([CH2:35][CH2:36][CH3:37])[CH2:31][CH2:30]4)[O:25][C:24]3=[O:38])=[C:19]([F:39])[C:18]=2[F:40])=[C:13]([F:41])[C:12]=1[F:42])[CH3:9].[H-].C([Al+]CC(C)C)C(C)C>C(O)=O>[CH2:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]3[CH2:28][CH2:27][CH:26]([CH:29]4[CH2:30][CH2:31][CH:32]([CH2:35][CH2:36][CH3:37])[CH2:33][CH2:34]4)[O:25][CH:24]3[OH:38])=[C:19]([F:39])[C:18]=2[F:40])=[C:13]([F:41])[C:12]=1[F:42])[CH3:9]

Komponenten

5

Edukt 3

HCID 1140Toluene2×HCID 21225700DiisobutylaluminumhydrideHCID 585356163-(4'-Ethoxy-2,2',3,3'-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-one

Produkt 1

HCID 585356523-(4'-Ethoxy-2,2',3,3'-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-olAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

Toluene (20 ml) was added to 3-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-one (11) (2.35 g) prepared in the ninth step. A toluene solution of diisobutylaluminum hydride (0.99 M; 9.6 ml) was added dropwise at −50° C. or lower, and the stirring was continued for 3 hours. The reaction mixture was poured into a 10% aqueous solution of formic acid (50 ml) to give two layers. The water layer was extracted with toluene (20 ml) twice and the combined organic layer was washed with water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to leave 3-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-ol (12) (2.29 g) in 99% yield.

Aufarbeitung

  1. customprepared in the ninth step
  2. customto give two layers
  3. extractionThe water layer was extracted with toluene (20 ml) twice
  4. washthe combined organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-049b9a6afd59455d86d9e852754942a8
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389073B2

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