Triacetoxyperiodinane → 1-[5-Chloro-2-(4-chloro-benzyloxy)-benzyl]-5-methyl-1H-pyrazole-3-carbaldehyde
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[C:6]([CH:16]=1)[CH2:7][N:8]1[C:12]([CH3:13])=[CH:11][C:10]([CH2:14][OH:15])=[N:9]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)=[C:6]([CH:16]=1)[CH2:7][N:8]1[C:12]([CH3:13])=[CH:11][C:10]([CH:14]=[O:15])=[N:9]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of alcohol 4 (0.57 g, 1.3 mmol) and 0.5 M Dess-Martin periodinane (9.05 mL, 4.1 mmol) in CH2Cl2 (25 mL) was stirred under N2 atmosphere at RT for 3 h. The reaction mixture was quenched with a 10% aqueous solution of Na2S2O3 (10 mL) and extracted with more CH2Cl2 (10 mL). The organic layer was washed with water (10 mL), dried (Na2SO4) and the volatiles were removed in vacuo. The residue was purified by MPLC (5 g SiO2 cartridge, eluent 70% iso-hexane-30% CH2Cl2) to give aldehyde 5 0.3 g (64%).