Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH2:9][CH2:8][C:7](=[O:10])[C:6]=1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[H+].[B-](F)(F)(F)F>>[CH3:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:6]1[C:7](=[O:10])[CH2:8][CH2:9][CH:5]1[CH2:4][C:3]([O:2][CH3:1])=[O:16]Komponenten
Versuchsvorschrift
In a glove box under argon and at room temperature, 38 mg of [(COD)Ru(2-methylallyl)2 ] (0.12 mmole) and 36 mg (0.12 mmole) of (-)-Me-DuPHOS were dissolved in 5.38 g (24 mmole) of methyl-3-oxo-2-pentyl-1-cyclopentene-acetate in a glass beaker adapted for use in an autoclave which was equipped with a stirrer. Thereafter, 39 mg of HBF4 etherate (0.24 mmole; 32.7 μl, syringe) were gently added under stirring. After stirring for 4 h, 3.4 ml of this catalytic solution (containing about 0.075 mmole of catalyst) were transferred to another beaker, and another 8.38 g (37.4 mmole) of methyl 3-oxo-2-pentyl-1-cyclopentene-1-acetate (total amount about 53 mmole) were added to this. Working as previously described, the substrate was hydrogenated at a H2 pressure of 5×106Pa. The reaction was allowed to proceed for 20 h at room temperature. The autoclave was degassed, opened, and the catalyst was precipitated using pentane, filtered and the filtrate concentrated to obtain the desired Hedione®. The thus obtained product (yield 99% based on the above mentioned substrate) showed the following isomer ratios: cis/trans=97/3: (+)-cis/(-)-cis=80/20, 60% e.e.
Aufarbeitung
- customwas equipped with a stirrer
- stirringAfter stirring for 4 h
- customThe autoclave was degassed
- customthe catalyst was precipitated
- filtrationfiltered
- concentrationthe filtrate concentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-34b0a08d054d45ffb2c0407e2aec98f4
- Quelldatensatz
- uspto-grants-1999_02
- Patentnummer
- US05874600
Verknüpfte Notizen
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