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

HRID 1265635Notes

Reaction equation

HRID 1265635 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[CH:12][S:13][C:14]=2[CH2:15]Br)[CH:5]=1.CC([O-])=[O:20].[K+].CO.C[O-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[CH:12][S:13][C:14]=2[CH2:15][OH:20])[CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 517044Potassium AcetateHCID 10942334Sodium MethoxideHCID 696877023-(5-Bromomethyl-thiazol-4-yl)-benzoic acid methyl ester

Product 1

HCID 696886433-(5-Hydroxymethyl-thiazol-4-yl)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(5-Bromomethyl-thiazol-4-yl)-benzoic acid methyl ester was stirred in DMF (10 mL) together with KOAc (1.52 g) at 20° C. for 30 min. MeOH (20 mL) and NaOMe (0.84 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 (1:2) as eluent to give 3-(5-hydroxymethyl-thiazol-4-yl)-benzoic acid methyl ester (1.43 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-59e4add3a39c41a68be664d6119e8a98
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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