Tetrahydrofuran → Ethyl 4-(hydroxymethyl)-1,3-thiazole-2-carboxylate
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]([C:11](O)=[O:12])[N:10]=1)=[O:5])[CH3:2].C1COCC1>CO>[OH:12][CH2:11][C:9]1[N:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-(ethoxycarbonyl)-1,3-thiazole-4-carboxylic acid (2 g), boran-THF complex (1.0 M in THF, 45.2 ml) and THF (50 ml) was heated under reflux overnight. After MeOH (2.0 ml) was added to the mixture at the same temperature, the mixture was concentrated in vacuo to dryness. The residue was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (0.96 g) as a white solid.
Workup
- temperatureunder reflux overnight
- concentrationthe mixture was concentrated in vacuo to dryness
- customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc)
Sources & evidence
- ORD record
- ord-e496314232ef4df18834c018eb66ffb8
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365540B2
Reaction notes
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