Methanol → 3-(5-Hydroxymethyl-2-methyl-thiazol-4-yl)-benzoic acid methyl ester

HRID 1265631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1265631
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[C:12]([CH3:17])[S:13][C:14]=2[CH2:15]Br)[CH:5]=1.CC([O-])=[O:21].[K+].CO>CN(C=O)C>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[C:12]([CH3:17])[S:13][C:14]=2[CH2:15][OH:21])[CH:5]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 517044Potassium AcetateHCID 696886923-(5-Bromomethyl-2-methyl-thiazol-4-yl)-benzoic acid methyl ester

Produkt 1

HCID 696880433-(5-Hydroxymethyl-2-methyl-thiazol-4-yl)-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-(5-bromomethyl-2-methyl-thiazol-4-yl)-benzoic acid methyl ester was stirred in DMF (16 mL) together with KOAc (2.35 g) at 20° C. for 20 min. MeOH (32 mL) and naOMe (0.86 g) were added and stirring was continued at 50° C. for 30 min. The mixture was partitioned between AcOEt and brine and the organic layer was dried and evaporated. The residual oil was chromatographed on silica gel using AcOEt/hexane (1:1) as eluent to give 3-(5-hydroxymethyl-2-methyl-thiazol-4-yl)-benzoic acid methyl ester (2.93 g) as a white solid.

Aufarbeitung

  1. customThe mixture was partitioned between AcOEt and brine
  2. customthe organic layer was dried
  3. customevaporated
  4. customThe residual oil was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e47c8f9d2e404fd99a9e89886f22874e
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06544985B2

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