Water → 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-1,3-thiazole-2-carbaldehyde

To a solution of 1-[2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl]ethane-1,2-diol (1.50 g) in acetone (10 mL) were added water (1 mL) and pyridinium p-toluenesulfonate (0.52 g) and the mixture was stirred with heating under reflux overnight. The reaction mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give a crude product (1.20 g). To a solution of the obtained crude product (1.20 g) in acetone (80 mL) was added pyridinium p-toluenesulfonate (1.80 g), and the mixture was stirred with heating under reflux overnight. The reaction mixture was concentrated, the residue was dissolved in ethyl acetate, and the solution was washed with water. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (0.50 g, yield 34%) was obtained as a yellow oil from a fraction eluted with ethyl acetate-hexane (2:3, volume ratio). MS: 214 (MH+).

1. temperaturewith heating
2. temperatureunder reflux overnight
3. extractionThe reaction mixture was extracted with ethyl acetate
4. washthe ethyl acetate layer was washed with saturated brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. customto give a crude product (1.20 g)
8. stirringthe mixture was stirred
9. temperaturewith heating
10. temperatureunder reflux overnight
11. concentrationThe reaction mixture was concentrated
12. dissolutionthe residue was dissolved in ethyl acetate
13. washthe solution was washed with water
14. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
15. dry with materialdried (MgSO4)
16. concentrationconcentrated

ORD record

ord-03a7cb53cf9b453eb4599cf67fee72b6

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318746B2