Hydrochloric Acid → HCID 86698881, 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 method 2-(((tert-butyldimethylsilyl)oxy)methyl)oxazole-4-carboxylate (3.00 g, 11.05 mmol) in THF (110 mL) was treated with tetraisopropoxytitanium (IV) (3.27 mL, 11.05 mmol). To the resulting solution at rt, was added, over 30 min, via syringe pump, ethyl magnesium bromide (18.4 mL of a 3M sol. in ether, 55.27 mmol) and the resulting solution was stirred at rt for 3 h. EA (100 mL) and 1N HCl (50 mL) were added. The layers were separated and the aq. layer was extracted with EA (2×100 mL) and the combined org. layers were washed with sat. aq. sodium bicarbonate (200 mL), brine (200 mL). The org. layer was dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA) gave the title compound as a yellow oil: TLC: rf (4:1 hept-EA)=0.28. LC-MS-conditions 06: tR=0.92 min, [M+H]+=270.41.

Provenance & Evidence