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Iodoethane → HCID 10104944, Verbindung

HRID 654701
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 654701
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[O:12][CH2:13][O:14][CH3:15].[CH3:16][CH2:17]CCCC.C([Li])CCC.C(I)C>O1CCCC1.O>[CH2:16]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[O:12][CH2:13][O:14][CH3:15])[CH3:17]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6340IodoethaneHCID 8058HexaneHCID 10445672HCID 10445672, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 10104944HCID 10104944, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

6.9 g of 5-bromo-1-methoxymethoxy naphthalene was dissolved in 100 ml of anhydrous tetrahydrofuran and cooled to -60° C. 21.3 ml of a hexane solution containing 1.6M of n-butyl lithium was gradually added to the solution. After stirring at -40° C.--60° C. for one hour, the reaction solution was cooled to -65° C. and 4.2 ml of ethyl iodide was slowly dropped. After the dropping, the temperature was warmed upto the room temperature, water was added and the solution was extracted with ethyl acetate. After washing the extract with an aqueous saturated solution of sodium chloride and drying over anhydrous magnesium sulfate, the solvent was distilled off. When the residue was purified on silica gel column chromatography (7% ethyl acetate/hexane), 5.5 g of the above-captioned compound was obtained as a pale yellow oily product.

Aufarbeitung

  1. additionwas gradually added to the solution
  2. temperaturethe reaction solution was cooled to -65° C.
  3. additionwas added
  4. extractionthe solution was extracted with ethyl acetate
  5. washAfter washing the
  6. extractionextract with an aqueous saturated solution of sodium chloride
  7. dry with materialdrying over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customWhen the residue was purified on silica gel column chromatography (7% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-af44be6c136749f9978047ab68652ee4
Quelldatensatz
uspto-grants-1992_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05134111

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