Nitrogen → 1-(5-(Hydroxymethyl)isoxazol-3-yl)ethanone

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 1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-isoxazol-3-yl]-ethanone (1.99 g, 7.79 mmol) in ethylene glycol (8.69 mL) was treated with trimethylorthoformate (1.71 mL, 15.58 mmol) followed by LiBF4 (146 mg, 1.56 mmol). The reaction mixture was heated at 95° C. overnight. Sat. aq. NaHCO3 (50 mL) was added and the mixture was extracted with EA (2×50 mL). The combined org. extracts were washed with brine (2×50 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (40:60 EA-Hept) gave the title compound as a yellow oil. TLC:rf (40:60 EA-Hept)=0.25. LC-MS-conditions 02: tR=0.54 min.

Provenance & Evidence