Water → 1-(2,4-Dimethyl-5-thiazolyl)but-1-en-3-one

HRID 246806Notes

Reaction equation

HRID 246806 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH:8]=O)=[C:5]([CH3:7])[N:6]=1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:17][C:18](=[O:20])[CH3:19])C=CC=CC=1.O>CS(C)=O>[CH3:1][C:2]1[S:3][C:4]([CH:8]=[CH:17][C:18](=[O:20])[CH3:19])=[C:5]([CH3:7])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 150381-(Triphenylphosphoranylidene)acetoneHCID 27762492,4-Dimethyl-1,3-thiazole-5-carbaldehyde

Product 1

HCID 540027301-(2,4-Dimethyl-5-thiazolyl)but-1-en-3-oneYield 81.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2,4-dimethylthiazole-5-carboxaldehyde (2.0 g) and 1-triphenylphosphoranylidene-2-propanone (8.2 g) in dimethylsulphoxide (140 ml) was stirred at ambient temperature for 24 hr. The solution was poured into water (400 ml) and extracted with dichloromethane. The dried (Na2SO4) organic extract was evaporated and the residue was purified by column chromatography over silica with ethyl acetate/n-hexane (1:1 v/v) elution to give 1-(2,4-dimethyl-5-thiazolyl)but-1-en-3-one (2.1 g). Pmr spectrum (CDCl3 ; δ in ppm): 2.32 (3H, s); 2.49 (3H, s); 2.67 (3H, s); 6.30 (1H, d); 7.60 (1H, d).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe dried (Na2SO4)
  3. extractionorganic extract
  4. customwas evaporated
  5. customthe residue was purified by column chromatography over silica with ethyl acetate/n-hexane (1:1 v/v) elution

Sources & evidence

ORD record
ord-b3b94120d4584cda83ae804690d26762
Source dataset
uspto-grants-1987_11
Patent number
US04704157

Reaction notes

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