1,3-Propanediol → 2-(1,3-Dioxan-2-yl)thiazole

HRID 1814469Notes

Reaction equation

HRID 1814469 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].[CH2:8](O)[CH2:9][CH2:10][OH:11]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:7]1[CH2:8][CH2:9][CH2:10][O:11][CH:6]1[C:2]1[S:1][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 104421,3-PropanediolHCID 27349031,3-Thiazole-2-carbaldehyde

Product 1

HCID 225025592-(1,3-Dioxan-2-yl)thiazoleYield 73%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

2-Thiazolecarboxaldehyde (1 g) was dissolved in toluene (50 ml), followed by the addition of trimethylene glycol (3.36 g) and p-toluenesulfonic acid (17 mg). The resulting mixture was heated under reflux with a Dean-Stark apparatus for 4 hr. After cooling as it was, the reaction mixture was washed sequentially with an aqueous solution of saturated sodium bicarbonate and brine, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a brown solid (1.104 g, yield; 73%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux with a Dean-Stark apparatus for 4 hr
  3. temperatureAfter cooling as it
  4. washthe reaction mixture was washed sequentially with an aqueous solution of saturated sodium bicarbonate and brine
  5. dry with materialdried (over MgSO4)
  6. customevaporated
  7. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-66ea020f5386411ea0dea16c9f0f2b06
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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