Acetic Acid → (R)-2-Benzhydryloxirane

HRID 606991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606991
C1(C)C=CC=CC=1.C(O)(=[O:10])C.[CH:12]([CH:25]1[CH2:27][O:26]1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC(C1C=C(C=N[C@H]2[C@H](N=CC3C([O-])=C(C(C)(C)C)C=C(C(C)(C)C)C=3)CCCC2)C([O-])=C(C(C)(C)C)C=1)(C)C.[Co+2].O>[CH:12]([C@@H:25]1[CH2:27][O:26]1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:19]1([CH:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C@H:25]([OH:10])[CH2:27][OH:26])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

7

Edukt 3

HCID 176Acetic AcidHCID 1140TolueneHCID 125490582-(Diphenylmethyl)oxirane

Produkt 2

HCID 11789056(R)-2-BenzhydryloxiraneHCID 54762284(2S)-3,3-diphenyl-propane-1,2-diol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9873565cobaltous;2,4-ditert-butyl-6-[[(1R,2R)-2-[(3,5-ditert-butyl-2-oxido-phenyl)methyleneamino]cyclohexyl]iminomethyl]phenolateKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of (R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane diaminocobalt (II) (0.22 g, 0.37 mmol, 0.8%), toluene (5 ml), and acetic acid (0.044 g, 0.74 mmol) was stirred for 1 h at room temperature. The solvent was removed in vacuo and the residue was dried. 2-Benzhydryl-oxirane (9.6 g, 45.7 mmol) was added in one portion and stirred, the mixture was then cooled by means of an ice-bath. H2O (0.58 g, 32 mmol) was slowly added over a 30-min period. After water addition, the ice bath was removed and the reaction mixture was stirred at room temperature for 72 h. Compounds were separated via flash chromatography on silica gel column to give (2R)-2-benzhydryl-oxirane (23a) 4.5 g ([α]D=(+)9.58, c=1, MeOH) and (2S)-3,3-diphenyl-propane-1,2-diol 24 3.53 g ([α]D=(+)48, c-=1, MeOH, ee=97%). The proton and carbon NMR data of (2R)-2-benzhydryl-oxirane was identical to the racemate 2-benzhydryl-oxirane.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue was dried
  3. stirringstirred
  4. temperaturethe mixture was then cooled by means of an ice-bath
  5. customthe ice bath was removed
  6. stirringthe reaction mixture was stirred at room temperature for 72 h
  7. customCompounds were separated via flash chromatography on silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-09295d6f76c343b49b3d8fca8af1209e
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915433B2

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