Thionyl Chloride → 4-(3-(tert-butyldimethylsilyloxy)-alpha-chlorobenzyl)-N,N-diethylbenzamide
Reaction equation
S(Cl)([Cl:3])=O.[Si:5]([O:12][C:13]1[CH:14]=[C:15]([CH:31]=[CH:32][CH:33]=1)[CH:16]([C:18]1[CH:30]=[CH:29][C:21]([C:22]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=1)O)([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6]>ClCCl>[Si:5]([O:12][C:13]1[CH:14]=[C:15]([CH:31]=[CH:32][CH:33]=1)[CH:16]([C:18]1[CH:30]=[CH:29][C:21]([C:22]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=1)[Cl:3])([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6]Participants
4
Procedure
Thionyl chloride (5.3 mL, 0.075 mol) was added to a solution of the benzhydryl alcohol from above (19.75 g, 0.048 mol) in 350 mL of dichloromethane. After stirring at room temperature overnight the solvent was evaporated, the residue was redissolved in toluene and again evaporated to drive off excess thionyl chloride and afford crude 4-(3-(tert-butyldimethylsilyloxy)-α-chlorobenzyl)-N,N-diethylbenzamide.