4-(1,2,3-Thiadiazol-4-yl)benzaldehyde → 1-[4-(1,2,3-Thiadiazol-4-yl)phenyl]ethanol

HRID 216332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216332
[CH3:1][Mg]Cl.[S:4]1[CH:8]=[C:7]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)[N:6]=[N:5]1>O1CCCC1>[S:4]1[CH:8]=[C:7]([C:9]2[CH:10]=[CH:11][C:12]([CH:13]([OH:14])[CH3:1])=[CH:15][CH:16]=2)[N:6]=[N:5]1

Komponenten

4

Edukt 2

HCID 27764534-(1,2,3-Thiadiazol-4-yl)benzaldehydeHCID 178418332HCID 178418332, Verbindung

Produkt 1

HCID 686676741-[4-(1,2,3-Thiadiazol-4-yl)phenyl]ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Methylmagnesium chloride (3 M in tetrahydrofuran) (0.83 mL, 2.5 mmol) was added to a −78° C. solution of 4-(1,2,3-thiadiazol-4-yl)benzaldehyde (473 mg, 2.5 mmol) in tetrahydrofuran (10 mL). After stirring at −78° C. for 2 h, the reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% ethyl acetate/hexane afforded 1-[4-(1,2,3-thiadiazol-4-yl)phenyl]ethanol.

Aufarbeitung

  1. customthe reaction mixture was quenched with saturated aqueous ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9a84652538d347e2ac624294d371ab00
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193228B2

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