Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate → (2-Bromo-4-methylthiazol-5-yl)methanol

HRID 2233310Notes

Reaction equation

HRID 2233310 reaction equation
[BH4-].[Na+].C([O:5][C:6]([C:8]1[S:12][C:11]([Br:13])=[N:10][C:9]=1[CH3:14])=O)C>C(O)C.O>[Br:13][C:11]1[S:12][C:8]([CH2:6][OH:5])=[C:9]([CH3:14])[N:10]=1

Participants

5

Reactant 2

HCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 59295463(2-Bromo-4-methylthiazol-5-yl)methanolYield 98.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

sodium borohydride (1.2 g, 31.2 mmol) is carefully added to a solution of 2-Bromo-4-methyl-thiazole-5-carboxylic acid ethyl ester (3.6 g, 15.6 mmol) in ethanol (100 mL) and water (1 mL) and stirred at room temperature for twelve hours. The solvent is carefully removed under reduced pressure, the residue is taken up in ethylacetate and washed with water. The organic phase is separated and dried over MgSO4. The organic solvent is removed under reduced pressure to give 3.2 g of (2-Bromo-4-methyl-thiazol-5-yl)-methanol, which was used without further purification.

Workup

  1. customThe solvent is carefully removed under reduced pressure
  2. washwashed with water
  3. customThe organic phase is separated
  4. dry with materialdried over MgSO4
  5. customThe organic solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-0126dbe6ec424ef7b6a4942e2ba2dd08
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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