Imidazole → HCID 67958930, compound

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methyl 2-(hydroxymethyl)oxazole-4-carboxylate (12.00 g, 76.37 mmol) in THF (360 mL) was treated with imidazole (10.40 g, 152.75 mmol) followed by tert-butyldimethylsilyl chloride (23.02 g, 152.75 mmol) and the resulting mixture was stirred at rt for 2.5 h. EA (360 mL) and sat. aq. NH4Cl (360 mL) were added. The layers were separated and the aq. layer was extracted with EA (360 mL). The combined org. layers were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (7:3 hept-EA) gave the title compound as a white solid: TLC: rf (7:3 hept-EA)=0.44. LC-MS-conditions 06: tR=0.98 min, [M+H]+=272.38.

Provenance & Evidence