5-Methylthiazole-4-carbaldehyde → α,5-Dimethyl-4-thiazolemethanol

HRID 577243Notes

Reaction equation

HRID 577243 reaction equation
[CH3:1][C:2]1[S:6][CH:5]=[N:4][C:3]=1[CH:7]=[O:8].[CH3:9][Mg]Br>C1COCC1>[CH3:1][C:2]1[S:6][CH:5]=[N:4][C:3]=1[CH:7]([OH:8])[CH3:9]

Participants

4

Reactant 2

HCID 110946275-Methylthiazole-4-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 21313043α,5-Dimethyl-4-thiazolemethanolYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 5-methyl-1,3-thiazole-4-carbaldehyde (1.0 g, 79 mmol) in anhydrous THF (30 mL) was added a solution of methyl magnesium bromide (3M in diethyl ether; 6 mL, 18 mmol). The reaction mixture was stirred at room temperature for 2 hours, and the mixture was then quenched with a saturated solution of ammonium chloride (20 mL). The mixture was extracted with EtOAc (3×30 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording 1-(5-methyl-1,3-thiazol-4-yl)ethan-1-ol (1.0 g, 63%). The product was used without further purification.

Workup

  1. customthe mixture was then quenched with a saturated solution of ammonium chloride (20 mL)
  2. extractionThe mixture was extracted with EtOAc (3×30 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-91b746c6bf9a4eb69a4b4a3120ca5140
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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