Thionyl Chloride → 4-(3-(tert-butyldimethylsilyloxy)-alpha-chlorobenzyl)-N,N-diethylbenzamide

HRID 929631

Reaction equation

HRID 929631 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

Reactant 2

HCID 24386Thionyl ChlorideHCID 223500144-((3-((Tert-butyldimethylsilyl)oxy)phenyl)(hydroxy)methyl)-N,N-diethylbenzamide

Product 1

HCID 223500364-(3-(tert-butyldimethylsilyloxy)-alpha-chlorobenzyl)-N,N-diethylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. customwas evaporated
  2. dissolutionthe residue was redissolved in toluene
  3. customagain evaporated

Sources & evidence

ORD record
ord-6defa958244f489a855c1717563d37f9
Source dataset
uspto-grants-2016_03
Patent number
US09296707B2

Linked notes

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