Ethyl Acetate → 2-(N,N-Diethylamino)-4-(hydroxymethyl)thiazole
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]([C:12]1[S:13][CH:14]=[C:15]([C:17](OCC)=[O:18])[N:16]=1)[CH2:10][CH3:11])[CH3:8].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C1COCC1>[CH2:7]([N:9]([C:12]1[S:13][CH:14]=[C:15]([CH2:17][OH:18])[N:16]=1)[CH2:10][CH3:11])[CH3:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of 3.14 ml of lithium aluminum hydride in toluene was diluted in a dry flask under N2 atmosphere with 30 ml of THF. The resulting mixture was cooled to 0° C. and treated dropwise with a solution of 1.43 g (6.28 mmol) of ethyl 2-(N,N-diethylamino)thiazole-4-carboxylate in 5 ml of THF. After addition, the solution was allowed to warm slowly to ambient temperature, stirred for 1 h, recooled to 0° C., and treated with a small amount of aqueous Rochelle's salt followed by ethyl acetate. After stirring, the slurry was filtered, washed with additional ethyl acetate, and the combined filtrates were concentrated in vacuo. The residue was purified by silica gel chromatography using methanol in chloroform to provide 0.864 g (73%) of the desired compound, Rf 0.17 (4% methanol in chloroform). Mass spectrum: (M+H)+ =187.
Workup
- additionAfter addition
- temperatureto warm slowly to ambient temperature
- customrecooled to 0° C.
- stirringAfter stirring
- filtrationthe slurry was filtered
- washwashed with additional ethyl acetate
- concentrationthe combined filtrates were concentrated in vacuo
- customThe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-b0d75e6ee67840ea8b4ff5b07709fc98
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616720
Reaction notes
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