Reaktionsgleichung
[C:1]([C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15]C)[CH:10]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2].B(Br)(Br)Br>ClCCl>[C:1]([C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a dichloromethane (80 ml) solution of 4-cyano-4-(3-methoxyphenyl)-3,4,5,6-tetrahydro-2H-pyran (2.32 g, 10.35 mmol) cooled to 0° C. was added boron tribromide (3.15 ml, 33.3 mmol) dropwise over 10 min. The ice-bath was removed and the reaction mixture stirred at ambient temperature for 19 h, and then at reflux for 4 h. The reaction mixture was cooled and poured into water (150 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (50 ml×3). The combined organic extracts were washed with brine (50 ml), dried (MgSO4) and concentrated in vacuo. The crude product was crystallized from isopropyl ether to afford titled compound as off-white solids (1.43 g, 66%).
Aufarbeitung
- customThe ice-bath was removed
- temperatureat reflux for 4 h
- temperatureThe reaction mixture was cooled
- additionpoured into water (150 ml)
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with ethyl acetate (50 ml×3)
- washThe combined organic extracts were washed with brine (50 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe crude product was crystallized from isopropyl ether
Quellen und Nachweise
- ORD-Eintrag
- ord-1971f387252f422bb3176677c9bfffff
- Quelldatensatz
- uspto-grants-1999_03
- Patentnummer
- US05883106
Verknüpfte Notizen
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