Hydrochloric Acid → [5-(4-Fluorophenyl)-1,2,3-thiadiazol-4-yl]methanol

HRID 30627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30627
[H-].C([Al+]CC(C)C)C(C)C.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:22][N:21]=[N:20][C:19]=2[C:23](OC)=[O:24])=[CH:14][CH:13]=1.Cl>O1CCCC1>[F:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[S:22][N:21]=[N:20][C:19]=2[CH2:23][OH:24])=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 69207857Methyl 5-(4-fluorophenyl)-1,2,3-thiadiazole-4-carboxylate

Produkt 1

HCID 69206022[5-(4-Fluorophenyl)-1,2,3-thiadiazol-4-yl]methanolAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Diisobutylaluminum hydride (1.5N toluene solution, 10 ml) was added to a solution of methyl 5-(4-fluorophenyl)-1,2,3-thiadiazole-4-carboxylate (1.19 g) in tetrahydrofuran (30 ml) at 0° C. and the mixture was stirred at 0° C. for 1 hr. The reaction mixture was poured into an aqueous dilute hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give [5-(4-fluorophenyl)-1,2,3-thiadiazol-4-yl]methanol (0.80 g, yield 76%) as a yellow oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c2b1b18a4158432dbb85475ba25d74f1
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423159B2

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