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4-Ethylbenzaldehyde → HCID 69220512, Verbindung

HRID 2116497
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2116497
Br[C:2]1[C:7]([O:8][CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])(C)(C)C.[CH2:25]([C:27]1[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=1)[CH3:26].[Cl-].[NH4+]>C1COCC1.CCCCC>[CH2:25]([C:27]1[CH:34]=[CH:33][C:30]([CH:31]([C:2]2[C:7]([O:8][CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:6][CH:5]=[CH:4][N:3]=2)[OH:32])=[CH:29][CH:28]=1)[CH3:26]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 208614-EthylbenzaldehydeHCID 25517Ammonium ChlorideHCID 23103610HCID 23103610, VerbindungHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 69220512HCID 69220512, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8003
Pentane
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Next, to a solution of 2-bromo-3-[2-(triethylsilyl)ethoxymethoxy]pyridine (2.0 g, 6.57 mmol) in THF (22 mL), a 1.47 M n-pentane solution of tert-butyllithium (9.6 mL, 14.1 mmol) was slowly added dropwise at −78° C. After 20 minutes, a solution of 4-ethylbenzaldehyde (1.0 g, 7.45 mmol) in THF (5 mL) was added dropwise to the reaction mixture. After stirring at −78° C. for 10 minutes, the reaction mixture was warmed to room temperature and saturated aqueous ammonium chloride was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 4-ethylphenyl-[3-[2-(triethylsilyl)ethoxymethoxy]]pyridin-2-yl-methanol (0.89 g, 38%).

Aufarbeitung

  1. temperaturethe reaction mixture was warmed to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-7449f885ebfe4d5eb0fe454eeef33e02
Quelldatensatz
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07439232B2

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