Hydrochloric Acid → 1-[5-(tert-Butyl-dimethyl-silanyloxymethyl)-isoxazol-3-yl]-ethanol

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 5-(tert-butyl-dimethyl-silanyloxymethyl)-isoxazole-3-carbaldehyde (1.74 g, 7.22 mmol) in CH2Cl2 (72.0 mL) was treated at 0° C. with trimethylaluminum (22.0 mL of a 1M solution in heptane, 22.0 mmol). The reaction mixture was then stirred at 0° C. for 50 min. CH2Cl2 (80.0 mL) followed by sat. aq. NH4Cl (80 mL) were then added. The mixture was then treated with 1N HCl (50 mL) and the aq. layer was extracted with CH2Cl2 (100 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a colorless oil: TLC:rf (7:3 hept-EA)=0.32. LC-MS-conditions 02: tR=1.01 min, [M+H]+=258.41.

Provenance & Evidence