Reaktionsgleichung
C([Li])(CC)C.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1.[CH3:21][C:22]([CH3:33])([C:28](OCC)=[O:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C1COCC1>[CH2:26]([O:25][C:23](=[O:24])[C:22]([CH3:33])([CH3:21])[C:28]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)=[O:29])[CH3:27]Komponenten
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
sec-Butyl lithium (5.85 mL, 7.6 mmol) was added to a solution of 1-bromo-4-benzyloxy-benzene (2.0 g, 7.6 mmol) in THF (10 mL) cooled to −78° C. under nitrogen. The reaction was stirred for 1 h and diethyl dimethylmalonate (4.29 g, 22.8 mmol) was added rapidly. This was stirred for an additional 0.5 h and then allowed to warm to room temperature. The reaction was partitioned between ethyl acetate and 1 N HCl. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by flash column chromatography (FCC) on silica gel eluting hexane:ethyl acetate (90: 10, v:v) to give 3-(4-benzyloxy-phenyl)-2,2-dimethyl-3-oxo-propionic acid ethyl ester (1.25 g, 50%) as an oil. MS found: (M+H)+=327.
Aufarbeitung
- stirringThis was stirred for an additional 0.5 h
- temperatureto warm to room temperature
- customThe reaction was partitioned between ethyl acetate and 1 N HCl
- washThe organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customto give an oil
- customThe product was purified by flash column chromatography (FCC) on silica gel
- washeluting hexane:ethyl acetate (90: 10, v:v)
Quellen und Nachweise
- ORD-Eintrag
- ord-5359d81de4724a08af69adbf01961d95
- Quelldatensatz
- uspto-grants-2006_09
- Patentnummer
- US07102008B2
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