Hydrochloric Acid → 5-(2-Methyl-[1,3]dioxolan-2-yl)-thiazole-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-bromo-5-(2-methyl-[1,3]dioxolan-2-yl)thiazole (5.00 g, 20.00 mmol) in dry Et2O (40 mL) was added to a n-BuLi (8.40 mL of a 2.5M solution in hexanes, 21.00 mmol) at −78° C. The reaction mixture was then stirred for 30 min at −78° C. before DMF (2.5 mL, 32.29 mmol) was added dropwise. The reaction mixture was stirred at −60° C. for 1 h. Sat. aq. NH4Cl (100 mL) was added, followed by aq. 1N HCl (50 mL). The layers separated and the aq. layer extracted with Et2O (5×). The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to give the title compound as an orange oil. TLC:rf (1:1 hept-EA)=0.50. LC-MS-conditions 01: tR=0.78 min; [M+H]+=199.93.

Provenance & Evidence