Hydrochloric Acid → 2,3-Dihydroimidazo[2,1-b][1,3]thiazole-6-carbaldehyde

Temperature

-70 °C

Ethyl 2,3-dihydroimidazo[2,1-b]thiazole-6-carboxylate (4.2 g; 21.21 mmol) was dissolved in dry dichloromethane (150 ml) and cooled to −70° C. under a stream of dry argon. This solution was treated with a solution of diisobutylaluminium hydride in toluene (1.5M, 26.9 ml, 2 equivalents) over 40 minutes at −70° C. The reaction mixture was stirred at −70° C. for a further 0.5 h. Water (10 ml) was added and the mixture stirred at ambient temperature for 0.5 hr. The mixture was acidified with 5M HCl, filtered through a celite pad and the pad further washed with dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulphate and evaporated to dryness. Chromatography on silica gel, eluting with ethyl acetate, gave the title compound (1.4 g, 43%).

1. stirringthe mixture stirred at ambient temperature for 0.5 hr
2. filtrationfiltered through a celite pad
3. washthe pad further washed with dichloromethane
4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
5. customevaporated to dryness
6. washChromatography on silica gel, eluting with ethyl acetate

ORD record

ord-90457985ccc9454da0a5721f10389568

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06472383B1