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Sodium Iodide → Tert-butyl[2-chloro-1-(iodomethyl)ethoxy]dimethylsilane

HRID 1398133
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1398133
CC1C=CC(S(O[CH2:12][CH:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:14][Cl:15])(=O)=O)=CC=1.[I-:24].[Na+]>CC(C)=O>[C:20]([Si:17]([O:16][CH:13]([CH2:12][I:24])[CH2:14][Cl:15])([CH3:19])[CH3:18])([CH3:23])([CH3:22])[CH3:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 866629712-{[Tert-butyl(dimethyl)silyl]oxy}-3-chloropropyl 4-methylbenzenesulfonate

Produkt 1

HCID 86662972Tert-butyl[2-chloro-1-(iodomethyl)ethoxy]dimethylsilaneAusbeute 74,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 2-{[tert-butyl(dimethyl)silyl]oxy}-3-chloropropyl 4-methylbenzenesulfonate (20.3 g) in acetone (200 mL) was added sodium iodide (19.7 g), and the mixture was stirred at 80° C. for 3 hr. The reaction mixture was concentrated, water was added to the residue, and the mixture was extracted with hexane. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (13.4 g).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue
  3. extractionthe mixture was extracted with hexane
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-139e8e51496a4863ac683f140d3771c7
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08901309B2

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