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

HRID 929631

Reaktionsgleichung

Reaktionsgleichung von HRID 929631
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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-6defa958244f489a855c1717563d37f9
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296707B2

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