Nitrogen → HCID 131730012, 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-(tert-butyl-dimethyl-silanyloxymethyl)-oxazole-4-carboxylic acid ethyl ester (410 mg, 1.43 mmol) in THF (10.0 mL) was treated at 0° C. with DiBAL (5.70 mL of a 1M sol in toluene, 5.70 mmol) and the reaction mixture was stirred for 45 min at 0° C. The reaction mixture was then diluted with EA (5.0 mL), sat. aq. Rochelle's salt (20.0 mL) was added and the mixture stirred at rt for 2 h. The layers were separated and the aq. layer extracted with EA (3×20 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow solid. TLC: rf (EA)=0.59. LC-MS-conditions 02: tR=0.94 min; [M+H]+=244.46.

Provenance & Evidence