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Hydrochloric Acid → (3-Chloro-4-methylthiophen-2-yl)methanol

HRID 502942
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 502942
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:12]([CH3:13])=[CH:11][S:10][C:9]=1[C:14](OC)=[O:15].Cl>C1COCC1>[Cl:7][C:8]1[C:12]([CH3:13])=[CH:11][S:10][C:9]=1[CH2:14][OH:15]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 2777567Methyl 3-chloro-4-methylthiophene-2-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 59767697(3-Chloro-4-methylthiophen-2-yl)methanolAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Lithium aluminum hydride (1.35 g) was added to a THF (50 ml) solution of methyl 3-chloro-4-methylthiophene-2-carboxylate (3.40 g) at 0° C., followed by stirring at 0° C. for 20 minutes. An 1M aqueous hydrochloric acid solution was added to the reaction solution and the whole was stirred at room temperature for 1 hour. The solution was filtered and, after ethyl acetate was added, the organic layer was separated. Furthermore, the organic layer washed with brine and, after drying over anhydrous sodium sulfate and filtration, the solvent was removed by evaporation under reduced pressure. The resulting crude product was purified by column chromatography (hexane:ethyl acetate=4:1) to obtain 2.68 g of (3-chloro-4-methyl-2-thienyl)methanol (pale yellow oil).

Aufarbeitung

  1. stirringthe whole was stirred at room temperature for 1 hour
  2. filtrationThe solution was filtered
  3. additionafter ethyl acetate was added
  4. customthe organic layer was separated
  5. washFurthermore, the organic layer washed with brine
  6. dry with materialafter drying over anhydrous sodium sulfate and filtration
  7. customthe solvent was removed by evaporation under reduced pressure
  8. customThe resulting crude product was purified by column chromatography (hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-10c891dbc6f84eb99077cbf9ea87afca
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07776897B2

Notizen zur Reaktion

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