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

HRID 1265631Notes

Reaction equation

HRID 1265631 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e47c8f9d2e404fd99a9e89886f22874e
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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