Sodium Chloride → (1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol

HRID 368903

Reaktionsgleichung

Reaktionsgleichung von HRID 368903
C([C@@H:6]([C@H:8]([C:10]([O:12][CH2:13]C)=O)[OH:9])O)(OCC)=O.C(OO)(C)(C)C.[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1C(=C)[C@@H](O)C.[OH-].[Na+].[Na+].[Cl-].[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[C@:10]1([O:12][CH2:13]1)[C@@H:8]([OH:9])[CH3:6]

Komponenten

9

Edukt 6

HCID 5234Sodium ChlorideHCID 6410tert-Butyl hydroperoxideHCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 6993580Diethyl tartrateHCID 15130435(2S)-3-(2,4-Difluorophenyl)-3-buten-2-ol

Produkt 1

HCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026Titanium isopropoxideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

To a solution of diethyl L(+)-tartrate (32.2 ml, 0.188 mole) in dry CH2Cl2 (5 L) is added activated 3A° molecular sieve powder (120 g) and cooled the mixture to -5 ° C. Added a solution of titanium (IV) isopropoxide (120 ml, 0.4 mole) followed by t-butyl hydroperoxide (312 ml of 5-6M solution in decane) and continue to stir at -5 ° C. for 25 minutes. To this mixture, a solution of crude 6a in CH2Cl2 (400 ml) is added and stirred for 12 hours at 5° C. Cooled the reaction mixture to -40° C., added 280 ml of 30% aq. NaOH solution saturated with NaCl and the mixture is allowed to warm to 10° C. Added 250 g of MgSO4, 80 g of celite and continued to stir at 10° C. for 30 minutes. The mixture is suction-filtered over celite. To the filtrate toluene (4 L) and 3 L of ether are added and insoluble material removed by filtration. The filtrate is evaporated under reduced pressure to give the crude 7a as oil.

Aufarbeitung

  1. stirringstirred for 12 hours at 5° C
  2. temperatureCooled the reaction mixture to -40° C.
  3. temperatureto warm to 10° C
  4. stirringto stir at 10° C. for 30 minutes
  5. filtrationThe mixture is suction-filtered over celite
  6. additionTo the filtrate toluene (4 L) and 3 L of ether are added
  7. custominsoluble material removed by filtration
  8. customThe filtrate is evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d643c81a52ac4b678f971e3e61537779
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133485

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