Hydrochloric Acid → HCID 69098014, Verbindung
Reaktionsgleichung
[CH2:1]1[C:3]2([CH2:8][C:7](=[O:9])[O:6][C:5](=[O:10])[CH2:4]2)[CH2:2]1.[CH3:11][Mg]Br.CC1CCCO1.Cl>O1CCCC1.[Cu]Cl.C(OC)(C)(C)C.O>[O:9]=[C:7]([CH3:11])[CH2:8][C:3]1([CH2:4][C:5]([OH:6])=[O:10])[CH2:2][CH2:1]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 4
Reaktionsbedingungen
- Temperatur
- -20 °C
Versuchsvorschrift
To a solution of 4.4 g 6-oxa-spiro[2.5]octane-5,7-dione (31 mmole) in 66 ml tetrahydrofuran are added 600 mg copper(I)chloride (6 mmole, 0.2 eq). The mixture is cooled to −20° C. and 9.8 ml of methylmagnesium bromide in 2-methyl tetrahydrofuran (3.2 M solution in 2-methyl tetrahydrofuran, 31 mmole, 1.0 eq) are added dropwise over 0.5 hours. The mixture is warmed to room temperature and stirred for 2 hours. 66 ml of water are added and the mixture is acidified to pH 3.0 by addition of 20.4 g of 2 M hydrochloric acid. 50 ml of methyl tert-butyl ether are added and the phases are separated. The aqueous phase is extracted again with 50 ml of methyl tert-butyl ether and the combined organic phases are washed with 20 ml of brine and concentrated to dryness. The resulting crude product is directly used in the next step (esterification to [1-(2-oxo-propyl)-cyclopropyl]-acetic acid methyl ester).
Aufarbeitung
- temperatureThe mixture is warmed to room temperature
- customthe phases are separated
- extractionThe aqueous phase is extracted again with 50 ml of methyl tert-butyl ether
- washthe combined organic phases are washed with 20 ml of brine
- concentrationconcentrated to dryness
Quellen und Nachweise
- ORD-Eintrag
- ord-a0347d69968a45ba977e482e3d6ea224
- Quelldatensatz
- uspto-grants-2015_12
- Patentnummer
- US09212120B2
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