Nitrogen → HCID 86649487, compound

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-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazole (733 mg, 3.22 mmol) in dry THF (16 mL) at −78° C. was treated with t-butyllithium (2.62 mL of a 1.6M solution in pentane, 4.19 mmol) while keeping the temperature below −70° C. The reaction mixture was then stirred for 1 h at −40° C. DMF (0.50 mL, 6.45 mmol) was added dropwise at −78° C. The reaction mixture was allowed to warm up to rt and stirred for 2 h at rt. Water (30 mL) was added followed by sat. aq. NH4Cl (20 mL) and EA (20 mL), the layers separated and the aq. layer extracted with EA (2×30 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (1:4 EA-Hept) gave the title compound as a colorless oil. TLC: rf (1:4 EA-Hept)=0.33. LC-MS-conditions 02: tR=1.08 min, [M+H]+=256.38.

Provenance & Evidence