Reaktionsgleichung
S(C)C.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([Mg]Br)=[CH:7][CH:6]=1.B(F)(F)F.CCOCC.[CH2:22]([CH:24]1[CH2:29][C:28](=[O:30])[CH:27]=[CH:26][N:25]1[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH3:23].[NH4+].[Cl-].[NH4+].[OH-]>C1COCC1>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH:26]2[CH2:27][C:28](=[O:30])[CH2:29][CH:24]([CH2:22][CH3:23])[N:25]2[C:31]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[O:32])=[CH:7][CH:6]=1Komponenten
Edukt 6
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
CuBr.SMe2 (5.6 g, 27.2 mmol) was added to dry THF (64 mL). It was cooled to −78° C. 4-Chlorophenylmagnesium bromide (27.2 mL, 1 M in THF, 27.2 mmol) was added to the mixture slowly over 1 hr at −78° C. Then BF3.Et2O (3.44 mL, 27.2 mmol) was added and the mixture was stirred for 5 min. Then ketone 82 (4 g, 8.1 mmol) in THF (55 mL) was added slowly over 1 hr at −78° C. After 2 hr stirring at −78° C., an aqueous solution of NH4Cl/conc. NH4OH (1:1, 20%, 60 mL) was added. The mixture was warmed to rt and extracted with EtOAc (200 mL×3), The combined organic layers were washed with brine, dried and concentrated to a residue and purified by silica gel chromatography (0-40% EtOAc/hexanes) to afford pure 83 (1 g, 2.7 mmol, 33%) as a mixture of cis stereoisomers.
Aufarbeitung
- stirringAfter 2 hr stirring at −78° C.
- temperatureThe mixture was warmed to rt
- extractionextracted with EtOAc (200 mL×3)
- washThe combined organic layers were washed with brine
- customdried
- concentrationconcentrated to a residue
- custompurified by silica gel chromatography (0-40% EtOAc/hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-7b77112cbcbd41cea3bf4f3c5c428bda
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07732609B2
Verknüpfte Notizen
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