Triacetoxyperiodinane → 2-Bromo-5-ethoxy-4-methylbenzaldehyde
Reaktionsgleichung
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH2:10][CH3:11])=[CH:4][C:3]=1[CH2:12][OH:13].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOCC>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH2:10][CH3:11])=[CH:4][C:3]=1[CH:12]=[O:13]Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of (2-bromo-5-ethoxy-4-methylphenyl)methanol (2.30 g, 9.38 mmol) in DCM (40 mL) was added Dess-Martin periodinane (5.97 g, 14.08 mmol). The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ether and was then concentrated. The residue was taken up in ether and was washed with of a mixture of 10% aqueous Na2S2O3 and saturated aqueous NaHCO3 (1/1), water and brine. The aqueous washings were back-extracted with ether and the organic layer was washed with water and brine. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified on a silica gel column eluting with 5 to 10% EtOAc in hexanes to afford the title intermediate as a white solid