Nitrogen → 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 (780 mg, 3.12 mmol) in dry Et2O (10 mL) was added to a n-BuLi (1.25 mL of a 2.5M solution in hexanes, 3.13 mmol) solution in Et2O (10 mL) at −78° C. The reaction mixture was then stirred for 30 min at −78° C. before DMF (0.29 mL, 3.78 mmol) was added dropwise. The reaction mixture was allowed to warm up to −20° C. and stirred at this temperature for 20 min. Sat. aq. NH4Cl (10 mL) was added, the layers separated and the aq. layer extracted with Et2O (3×10 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (10:1 to 3:1 hept-EA) gave the title compound as a yellow oil. TLC:rf (1:1 hept-EA)=0.50. LC-MS-conditions 01: tR=0.78 min; [M+H]+=199.93.

Provenance & Evidence