Hydrochloric Acid → (4-Ethyl-2-methyl-1,3-thiazol-5-yl)methanol

HRID 591497Notes

Reaction equation

HRID 591497 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([CH3:11])[S:6][C:7]=1[C:8](O)=[O:9])[CH3:2].Cl>C1COCC1>[CH2:1]([C:3]1[N:4]=[C:5]([CH3:11])[S:6][C:7]=1[CH2:8][OH:9])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 146487654-Ethyl-2-methyl-1,3-thiazole-5-carboxylic acid

Product 1

HCID 37134637(4-Ethyl-2-methyl-1,3-thiazol-5-yl)methanolYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a borane tetrahydrofuran complex solution (1.2 M in THF, 5 mL) was added 4-ethyl-2-methylthiazole-5-carboxylic acid (400 mg) at 0° C. The mixture was stirred at 0° C. to room temperature under argon atmosphere overnight. To the mixture was added 1N HCl at room temperature, and the mixture was extracted with EtOAc. The organic layer was separated, washed successively with brine and water, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (125 mg).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with brine and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-0c58eb5110d94b3c996c563aa287aedd
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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