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Dichloromethane → (E)-7-(tert-butyldimethylsiloxy)-2-methylhept-2-enal

HRID 1433239
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1433239
C(N(CC)CC)C.C(Cl)Cl.[O:11]([CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[C:24](\[CH3:27])/[CH2:25][OH:26])[Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>CS(C)=O>[O:11]([CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[C:24](\[CH3:27])/[CH:25]=[O:26])[Si:12]([C:15]([CH3:17])([CH3:18])[CH3:16])([CH3:14])[CH3:13]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 23249620HCID 23249620, Verbindung

Produkt 1

HCID 11402629(E)-7-(tert-butyldimethylsiloxy)-2-methylhept-2-enalAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

After the addition of triethylamine (36.5 ml) to a methylene chloride solution (53 ml) of Alcohol 5 (13.6 g) and cooling to 0° C., a dimethylsulfoxide solution (53 ml) of SO3-pyridine (25 g) is added thereto at 0° C. and the whole is stirred for 1.5 hours. After stirring, the resultant solution is quenched using a buffer solution (5 ml) and the organic compound is extracted three times with ethyl acetate, followed by the wash of the organic layer in a saturated saline solution and drying over anhydrous sodium sulfate. After anhydrous sodium sulfate is filtered and the solvent is distilled off under reduced pressure, the residue is separated and purified by column chromatography to produce Aldehyde 6 (12.8 g) of 94% in yield.

Aufarbeitung

  1. stirringAfter stirring
  2. customthe resultant solution is quenched
  3. extractionthe organic compound is extracted three times with ethyl acetate
  4. washwash of the organic layer in a saturated saline solution
  5. dry with materialdrying over anhydrous sodium sulfate
  6. filtrationAfter anhydrous sodium sulfate is filtered
  7. distillationthe solvent is distilled off under reduced pressure
  8. customthe residue is separated
  9. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-aebe91789a304cd5b734e42dc19d992c
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07612213B2

Notizen zur Reaktion

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