Methanol → 2-(1,1-Dimethoxyethyl)thiazole

HRID 877363Notes

Reaction equation

HRID 877363 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6](=[O:8])[CH3:7].[CH3:9]C1C=CC(S(O)(=O)=O)=CC=1.[CH3:20][OH:21]>>[CH3:20][O:21][C:6]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)([O:8][CH3:9])[CH3:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 5201082-Acetylthiazole

Product 1

HCID 110739802-(1,1-Dimethoxyethyl)thiazoleYield 75.6%

Procedure

A mixture of 1-(1,3-thiazol-2-yl)ethanone (35 g, 0.28 mol), anhydrous p-TsOH (50 g, 0.29 mol) and trimethyl ortheformate (175 ml) in methanol (500 ml) was refluxed for 18 h. After concentration, the residue was partitioned between sat. NaHCO3 and ether. The organic layers were washed with brine, dried over Na2SO4 and concentrated to give 36 g (75.6%) of 2-(1,1-dimethoxyethyl)-1,3-thiazole as an oil.

Workup

  1. temperaturewas refluxed for 18 h
  2. concentrationAfter concentration
  3. customthe residue was partitioned between sat. NaHCO3 and ether
  4. washThe organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fb2a5368ff824a90b196b2e33722bc00
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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