Hydrochloric Acid → 3-Methyl-1-(2-methyl-5-phenylfuran-3-yl)butan-1-ol
Reaktionsgleichung
[CH3:1][CH:2]1[CH:6]=[CH:5][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(C=O)[O:3]1.[CH:15]1([Mg]Br)CCC1.[O:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.Cl.O>O1CCCC1>[CH3:22][CH:23]([CH3:15])[CH2:24][CH:25]([C:6]1[CH:5]=[C:4]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[O:3][C:2]=1[CH3:1])[OH:21]Komponenten
6
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of 2-methyl-5-phenylfuran-5-carbaldehyde (1.3 g) in tetrahydrofuran (30 mL) was added dropwise 1N cyclobutylmagnesium bromide-tetrahydrofuran solution (10.5 mL) at 0° C. and, after the completion of the dropwise addition, the mixture was stirred at 0° C. for 1 hr. The reaction mixture was treated with 1N hydrochloric acid, poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (0% ethyl acetate/hexane to 20% ethyl acetate/hexane) to give the title compound (1.5 g, 87%) as a yellow crystal.
Aufarbeitung
- additionafter the completion of the dropwise addition
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column (0% ethyl acetate/hexane to 20% ethyl acetate/hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-d3c8801d2bdd42cca3886c9f8fb96d91
- Quelldatensatz
- uspto-grants-2012_11
- Patentnummer
- US08309580B2
Notizen zur Reaktion
Wird geladen…