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Imidazole → 3-{[tert-Butyl(diphenyl)silyl]oxy}-2-fluoropropionic acid ethyl ester

HRID 1847019
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1847019
[CH2:1]([O:3][C:4](=[O:9])[CH:5]([F:8])[CH2:6][OH:7])[CH3:2].N1C=CN=C1.[Si:15](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:3][C:4](=[O:9])[CH:5]([F:8])[CH2:6][O:7][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 13572114Ethyl 2-fluoro-3-hydroxypropanoateHCID 86585896Sodium bicarbonate water

Produkt 1

HCID 867249473-{[tert-Butyl(diphenyl)silyl]oxy}-2-fluoropropionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A crude product of 2-fluoro-3-hydroxypropionic acid ethyl ester (13.06 g) was dissolved in dichloromethane (300 ml). Imidazole (17.2 g, 252.57 mmol) and tert-butyldiphenylsilyl chloride (25 ml, 96.14 mmol) were added to the solution under cooling on ice, and the reaction solution was stirred for 18 hours while raising the reaction solution temperature to room temperature. Saturated sodium bicarbonate water was added to the reaction solution and the resultant was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 17.98 g (three steps, 57%) of the title compound in the form of a colorless clear oily product.

Aufarbeitung

  1. temperatureunder cooling on ice
  2. extractionthe resultant was extracted with dichloromethane
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a23be69496cf4a2096d9246d8dc98172
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08952010B2

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