Tributylstannane → S(-)-1-(PENTAFLUOROPHENYL)ETHANOL

HRID 2249007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2249007
Br[CH2:2][C@@H:3]([C:5]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]([F:14])[C:6]=1[F:15])[OH:4].BrC(C1C(F)=C(F)C(F)=C(F)C=1F)CO.C([SnH](CCCC)CCCC)CCC>CCCCCC>[F:11][C:10]1[C:5]([C@@H:3]([OH:4])[CH3:2])=[C:6]([F:15])[C:7]([F:14])=[C:8]([F:13])[C:9]=1[F:12]

Komponenten

5

Edukt 3

HCID 5948TributylstannaneHCID 14645957HCID 14645957, VerbindungHCID 19995411HCID 19995411, Verbindung

Produkt 1

HCID 6993305S(-)-1-(PENTAFLUOROPHENYL)ETHANOLAusbeute 48,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 11.26 g of (R)-(-)-2-bromo-1-(pentafluorophenyl)ethanol containing 20% of 2-bromo-2-(pentafluorophenyl)ethanol obtained in Example 7 in 50 ml of hexane, was added 11.4 ml of tributyltin hydride at room temperature. After stirring for eight hours at 60° C., the reaction mixture was concentrated under reduced pressure, purified by silica gel column chromatography and distilled under reduced pressure to give 4.0 g of (S)-(-)-1-(pentafluorophenyl)ethanol having the following physical properties.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified by silica gel column chromatography
  3. distillationdistilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6cdc958240884f4d8223337fd7b62c25
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05041641

Notizen zur Reaktion

Wird geladen…