Triacetoxyperiodinane → [4-(Tert-butyldimethylsilanyloxy)-3-oxobutyl]carbamic acid tert-butyl ester
Reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28](=[O:43])[NH:29][CH2:30][CH2:31][CH:32]([OH:42])[CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])([CH3:26])([CH3:25])[CH3:24]>ClCCl>[C:23]([O:27][C:28](=[O:43])[NH:29][CH2:30][CH2:31][C:32](=[O:42])[CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:36])[CH3:37])([CH3:26])([CH3:24])[CH3:25]Participants
4
Procedure
To a solution of Dess-Martin periodinane (5.0 g, 11.8 mmol) in anhydrous dichloromethane (35 mL) at room temperature was added a solution of [4-(tert-butyldimethylsilanyloxy)-3-hydroxybutyl]carbamic acid tert-butyl ester (3.77 g, 11.8 mmol) in anhydrous dichloromethane. The resulting mixture was stirred at room temperature for one hour, evaporated in vacuo to one third of the initial volume and applied to a column packed with silica. Elution with ethyl acetate—petroleum ether solvent mixture afforded a colorless oil.