Acetone → 2-(2-nitrophenyl)-Thiazolo[5,4-b]pyridine-6-methanol

HRID 453279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453279
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][C:15]([C:19](OC)=[O:20])=[CH:14][N:13]=2)([O-:3])=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].CC(C)=O.[O-]S([O-])=O.[Na+].[Na+]>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][C:15]([CH2:19][OH:20])=[CH:14][N:13]=2)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 24437Sodium SulfiteHCID 21226445Aluminium lithium hydrideHCID 58551887Methyl 2-(2-nitrophenyl)thiazolo[5,4-b]pyridine-6-carboxylate

Produkt 1

HCID 573471802-(2-nitrophenyl)-Thiazolo[5,4-b]pyridine-6-methanolAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

A solution of methyl 2-(2-nitrophenyl)thiazolo[5,4-b]pyridine-6-carboxylate (1 eq) in THF was added over 8 h to a mixture of lithium aluminum hydride (LAH) (4.4 eq) in THF maintaining the internal temperature at −55° C. The reaction mixture was stirred an additional 4 h at −60° C. Acetone (18 eq) was added followed by sat. aq Na2SO3. The resultant solids were removed by filtration and rinsed with THF. The combined organics were concentrated in vacuo and the crude residue crystallized from CH2Cl2 to give (2-(2-nitrophenyl)thiazolo[5,4-b]pyridin-6-yl)methanol (50% yield).

Aufarbeitung

  1. customThe resultant solids were removed by filtration
  2. washrinsed with THF
  3. concentrationThe combined organics were concentrated in vacuo
  4. customthe crude residue crystallized from CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-08a366e350b048b09465e04033542f3f
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492401B2

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