Acetone → 1-(2-Methyl-5-thiazolyl)but-1-en-3-one

HRID 986720Notes

Reaction equation

HRID 986720 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[S:5][C:6]([CH:9]=O)=[CH:7][N:8]=1.[CH3:11][C:12]([CH3:14])=[O:13]>O>[CH3:3][C:4]1[S:5][C:6]([CH:9]=[CH:11][C:12](=[O:13])[CH3:14])=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 139347282-Methyl-1,3-thiazole-5-carbaldehyde

Product 1

HCID 541914301-(2-Methyl-5-thiazolyl)but-1-en-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

An aqueous solution of 2% sodium hydroxide (3 ml) was added to a solution of 2-methyl-thiazole-5-carboxaldehyde (2.5 g) in acetone (20 ml) and water (10 ml). The mixture was stirred for 24 hours at ambient temperature, diluted with water (150 ml) and extracted with chloroform (2×50 ml). The organic layer was washed with water then dried over anhydrous magnesium sulphate and filtered. Evaporation of the solvent gave 1-(2-methyl-5-thiazolyl)but-1-en-3-one as a low-melting point solid (1.4 g, 43%). Pmr spectrum (CDCl3 ; δ in ppm): 2.30 (3H, s); 2.72 (3H, s); 6.36 (1H, d); 7.56 (1H, d); 7.74 (1H, s).

Workup

  1. extractionextracted with chloroform (2×50 ml)
  2. washThe organic layer was washed with water
  3. dry with materialthen dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e003492912f542cda1f5da8ec54f064b
Source dataset
uspto-grants-1987_12
Patent number
US04715884

Reaction notes

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