Ethylene Glycol → 2-(1,3-Dioxolan-2-yl)-1,3-thiazole

HRID 1037977Notes

Reaction equation

HRID 1037977 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].[CH2:8](O)[CH2:9][OH:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1.CCOCC.CCOC(C)=O>[O:7]1[CH2:8][CH2:9][O:10][CH:6]1[C:2]1[S:1][CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 27349031,3-Thiazole-2-carbaldehyde

Product 1

HCID 152051582-(1,3-Dioxolan-2-yl)-1,3-thiazoleYield 133.7%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of thiazole-2-carbaldehyde (100 g, 0.88 mol), ethane-1,2-diol (164 g, 2.65 mol), p-toluenesulfonic acid monohydrate (50 g, 0.26 mol) in toluene (1000 mL) was refluxed overnight with azetropic removal of water. The mixture was cooled to rt, diluted with ether (1000 mL), and washed with sat. NaHCO3 solution (200 mL), brine (200 mL), dried (Na2SO4), and concentrated to give a yellow oil. Flash column chromatography (petroleum ether:EtOAc, 100:1 to 50:1) afforded 2-(1,3-dioxolan-2-yl)thiazole (185 g, 66%). 1H NMR (CDCl3, 300 MHz) δ 7.75 (s, 1H), 7.31 (s, 1H), 6.09 (s, 1H), 4.04 (m, 4H).

Workup

  1. washwashed with sat. NaHCO3 solution (200 mL), brine (200 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-0995cd0d22e34e74a19cf65ccbf82742
Source dataset
uspto-grants-2013_10
Patent number
US08546588B2

Reaction notes

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