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Water → HCID 86651747, Verbindung

HRID 1515090
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1515090
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[H-].[Na+].[F:16][C:17]([F:23])([F:22])[S:18](Cl)(=[O:20])=[O:19].O>C(OCC)C>[F:16][C:17]([F:23])([F:22])[S:18]([O:13][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:9]([F:11])([F:12])[F:10])(=[O:20])=[O:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79000Trifluoromethanesulfonyl chlorideHCID 2603991-(4-chlorophenyl)-2,2,2-trifluoroethanol

Produkt 1

HCID 86651747HCID 86651747, VerbindungAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283
Diethyl Ether
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-(4-Chlorophenyl)-2,2,2-trifluoroethanol (1.20 g, 5.70 mmol) was dissolved in diethyl ether (80 mL), and the resulting solution was cooled to 0° C. Then, 63% sodium hydride (217 mg, 5.70 mmol) was added thereto, and the resulting mixture was stirred for 1 hour. Thereafter, trifluoromethanesulfonyl chloride (0.910 mL, 8.55 mmol) was added dropwise thereto. Then, the temperature of the reaction solution was raised to room temperature, and the reaction solution was stirred for 2 hours. Water was added to the reaction solution, and the organic matter was extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 93:7 (v/v)), whereby the objective title compound was obtained as a colorless oily substance (495 mg, yield: 25%).

Aufarbeitung

  1. temperatureThen, the temperature of the reaction solution was raised to room temperature
  2. stirringthe reaction solution was stirred for 2 hours
  3. extractionthe organic matter was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated sodium chloride solution, then dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
  8. customwas obtained
  9. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 93:7 (v/v)), whereby the objective title compound
  10. customwas obtained as a colorless oily substance (495 mg, yield: 25%)

Quellen und Nachweise

ORD-Eintrag
ord-c0ff7490f9a94acaaa5356cb430f8244
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08222281B2

Notizen zur Reaktion

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