(R)-2-Benzhydryloxirane → (2S)-1,1-diphenyl-pent-4-ene-2-ol

HRID 606993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606993
[CH:1]([C@@H:14]1[CH2:16][O:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]([Mg]Br)=[CH2:18]>C1COCC1.[Cu]I>[C:2]1([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:14]([OH:15])[CH2:16][CH:17]=[CH2:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 11789056(R)-2-Benzhydryloxirane2×HCID 178418507HCID 178418507, Verbindung

Produkt 1

HCID 11390776(2S)-1,1-diphenyl-pent-4-ene-2-olAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

(2R)-2-benzhydryl-oxirane (0.5 g, 2.38 mmol) 23a was dissolved in dry THF (5 ml) and was added into a dry THF solution at −78° C. containing CuI (0.045 g, 0.24 mmol) and vinylmagnesium bromide (5.95 ml of 1.0M solution in THF, 5.95 mmol). The reaction mixture was stirred and allowed to reach room temperature over a period of 2h, and then quenched with saturated NH4Cl solution. The aqueous phase was extracted with ethyl acetate (3×30 ml). The combined organic phase was washed with brine and dried over anhydrous Na2SO4. The solvent was removed and the residue was purified by flash chromatography on silica gel (Hexane/Ethyl Ether=4:1) to give 0.4 g (2S)-1,1-diphenyl-pent-4-ene-2-ol (70%, [α]D=(−)25, c=1, MeOH).

Aufarbeitung

  1. customquenched with saturated NH4Cl solution
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×30 ml)
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was removed
  6. customthe residue was purified by flash chromatography on silica gel (Hexane/Ethyl Ether=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-97f420b978bd400da66a1de4670d2f68
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915433B2

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