Nitrogen → [5-(tert-Butyl-dimethyl-silanyloxymethyl)-isoxazol-3-yl]-methanol

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Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(tert-butyl-dimethyl-silanyloxymethyl)-isoxazole-3-carboxylic acid ethyl ester (5.77 g, 20.22 mmol) in THF (200 mL) was treated at −78° C. with DiBAL-H (40.00 mL of a 1M solution in THF, 40.43 mmol). The reaction mixture was stirred at this temperature for 1 h before to be allowed to warm to rt. The reaction mixture was poured onto Rochelle's salt (200 mL) and stirred at rt for 1 h. The aq. layer was extracted with EA (2×200 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (70:30 hept-EA) gave the title compound as a yellow oil: TLC:rf (70:30 hept-EA)=0.28. LC-MS-conditions 02: tR=0.99 min; [M+H]+=244.35.

Provenance & Evidence