Imidazole → 5-{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-oxazole-4-carboxylic acid methyl ester

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), 5-[3-(2-hydroxy-ethyl)-phenyl]-oxazole-4-carboxylic acid methyl ester (200 mg, 0.81 mmol) was dissolved in dry THF (5.0 mL). tert-Butyldimethylsilyl chloride (124 mg, 0.83 mmol) was added at 0° C. followed by imidazole (61 mg, 0.89 mmol). The reaction mixture was stirred at rt for 2 days. Sat. aq. NH4Cl (10 mL) and EA (10 mL) were added, the layers separated and the aq. layer extracted with EA (2×10 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (20:80 hept-EA) gave the title compound as a colorless oil. TLC: rf (20:80 hept-EA)=0.21. LC-MS-conditions 02: tR=1.19 min, [M+H]+=362.50.

Provenance & Evidence