Reaktionsgleichung
[CH3:1][C:2]([CH3:12])=[CH:3][CH:4]1[CH:6]([C:7](Cl)=[O:8])[C:5]1([CH3:11])[CH3:10].[CH3:13][O:14][CH2:15][C:16]1[C:23]([F:24])=[C:22]([F:25])[C:19]([CH2:20][OH:21])=[C:18]([F:26])[C:17]=1[F:27].N1C=CC=CC=1>O1CCCC1>[CH3:1][C:2]([CH3:12])=[CH:3][CH:4]1[CH:6]([C:7]([O:21][CH2:20][C:19]2[C:18]([F:26])=[C:17]([F:27])[C:16]([CH2:15][O:14][CH3:13])=[C:23]([F:24])[C:22]=2[F:25])=[O:8])[C:5]1([CH3:11])[CH3:10]Komponenten
Versuchsvorschrift
0.50 Gram of 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride {containing the stereoisomers in a ratio of (1R)-trans form: (1R)-cis form: (1S)-trans form: (1S)-cis form =32.5:17.5:32.5:17.5} was added to a mixture of 0.55 g of 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl alcohol, 0.23 g of pyridine and 7 ml of tetrahydrofuran under ice-cooling. The resulting mixture was heated to room temperature and stirred at room temperature for 8 hours. The reaction mixture was poured into about 20 ml of ice water and extracted twice with 40 ml of ethyl acetate. The combined ethyl acetate layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.74 g (yield: 80%) of 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylate (hereinafter referred to as the present compound 2).
Aufarbeitung
- customform
- custom(1R)-cis form: (1S)-trans form
- temperaturecooling
- extractionextracted twice with 40 ml of ethyl acetate
- washThe combined ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-0b83c81c934e454b91eb89f5553c1cda
- Quelldatensatz
- uspto-grants-2001_09
- Patentnummer
- US06294576B1
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