Methanol → 2-(1,1-Dimethoxyethyl)thiazole
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
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
- temperaturewas refluxed for 18 h
- concentrationAfter concentration
- customthe residue was partitioned between sat. NaHCO3 and ether
- washThe organic layers were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fb2a5368ff824a90b196b2e33722bc00
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987310B2
Reaction notes
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