Thionyl Chloride → {[tert-Butyl(diphenyl)silyl]oxy}acetyl Chloride

HRID 1766118

Reaktionsgleichung

Reaktionsgleichung von HRID 1766118
[Si:1]([O:18][CH2:19][C:20]([OH:22])=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:25])=O>C(Cl)Cl>[Si:1]([O:18][CH2:19][C:20]([Cl:25])=[O:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 111415642-((tert-Butyldiphenylsilyl)oxy)acetic acid

Produkt 1

HCID 19090360{[tert-Butyl(diphenyl)silyl]oxy}acetyl ChlorideAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a 500 ml round-bottom flask was mixed {[tert-butyl(diphenyl)silyl]oxy}acetic acid (17 g, 54.0 mmoles, 1 eq), thionyl chloride (11.7 g, 0.162 moles, 3 eq) and dry CH2Cl2 (120 ml, 0.45M). This mixture was refluxed for 5 hours. After cooling to room temperature the volatiles were removed in vacuo. The resulting residue was washed twice with toluene and the toluene was subsequently removed in vacuo to remove excess thionyl chloride. This resulted in 18 g (100%) of titled compound.

Aufarbeitung

  1. temperatureThis mixture was refluxed for 5 hours
  2. customwere removed in vacuo
  3. washThe resulting residue was washed twice with toluene
  4. customthe toluene was subsequently removed in vacuo
  5. customto remove excess thionyl chloride

Quellen und Nachweise

ORD-Eintrag
ord-71cb4c5f379f421eb599e83bc79b10af
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07229998B2

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