Ethylene Glycol → 2-Bromo-4-(1,3-dioxolan-2-yl)thiazole
Reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]=[O:8])[N:6]=1.[CH2:9](O)[CH2:10][OH:11]>C1(C)C=CC=CC=1>[Br:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]2[O:11][CH2:10][CH2:9][O:8]2)[N:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Bromothiazole-4-carbaldehyde (6.56 g,34.17 mmol) [A. T. Ung, S. G. Pyne/Tetrahedron: Asymmetry 9 (1998) 1395-1407] and ethylene glycol (5.72 ml, 102.5 mmol) were heated under reflux in toluene (50 ml), with a Dean and Stark trap fitted, for 18 hr. The product was concentrated and purified by column chromatography (15% ethyl acetate/hexane) to give the product as a yellow solid (6.03 g); m/z 236,238.
Workup
- customfitted, for 18 hr
- concentrationThe product was concentrated
- custompurified by column chromatography (15% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-6a84d2738cd840d5bfd5498824bb50d9
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07265123B2
Reaction notes
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