Nitrogen → HCID 131730004, compound

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of n-BuLi (4.3 mL of a 2.5 M solution in hexanes, 10.75 mmol) in dry Et2O (15 mL) was added a solution of 2-bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-thiazole (3.03 g, 9.83 mmol) in dry Et2O (10 mL) at −78° C. The reaction mixture was then stirred for 30 min at −78° C. before N,N-dimethylacetamide (1.9 mL, 20.43 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 1 h. Sat. aq. NH4Cl (20 mL) was added, the layers separated and the aq. layer extracted with Et2O (2×30 mL). 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 (2:1 hept-EA)=0.60. LC-MS-conditions 02: tR=1.14 min; [M+H]+=272.32.

Provenance & Evidence