Calcium Bromide → cis-(+/-)-4-Bromotetrahydro-2-[(phenylmethoxy)methyl]furan
Reaktionsgleichung
[Br:1][CH:2]([CH2:15]Br)[CH2:3][CH:4]([OH:14])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Ca+2].[OH-].[Br-].[Ca+2].[Br-]>CO.O>[Br:1][C@H:2]1[CH2:15][O:14][C@@H:4]([CH2:5][O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A solution of 10.0 g of product from Example 3 in 25 ml of methyl alcohol is diluted with 50 ml of distilled water. To this heterogeneous mixture is added 1.6 g of calcium hydroxide followed by 16.95 g of calcium bromide. The reaction is stirred vigorously while heating in an oil bath, at 100° C., for 24 hours. The internal temperature is maintained at 85° C. The reaction is cooled, extracted with methylene chloride, filtered thru diatomaceous earth and the layers partitioned. The organic layer is washed with water and saturated sodium chloride, dried and concentrated in vacuo to give 7.18 g of an oil. The oil is purified by chromatography (Silica Gel: 5% ethyl acetate/hexane) to give 2.82 g of the trans-isomer and 2.89 g of the cis-isomer.
Aufarbeitung
- temperatureThe internal temperature is maintained at 85° C
- temperatureThe reaction is cooled
- extractionextracted with methylene chloride
- filtrationfiltered
- customthe layers partitioned
- washThe organic layer is washed with water and saturated sodium chloride
- customdried
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-21a570ace2494572b7657700c817556a
- Quelldatensatz
- uspto-grants-1998_05
- Patentnummer
- US05750735
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