HCID 25131666, compound → HCID 25132009, compound

Participants

Reaction Steps

Methyl lithium (159 μL, 1.6 M solution in Et2O, 0.25 mmol) was added dropwise to a solution of 1-(4-(4-cyclohexylisoxazol-5-yl)phenyl)ethanone obtained above (57 mg, 0.21 mmol) in THF (2 mL) at 0° C. After stirring for 15 min, another 100μL of the methyl lithium solution was added to the reaction mixture. After being stirred for an additional 1 h at 0° C., the mixture was quenched with saturated aqueous NH4Cl and diluted with EtOAc. The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with NaCl, dried with magnesium sulfate, filtered and concentrated in vacuo to give a yellow oil. The crude material was purified by flash column chromatography (20%→40% EtOAc/hexanes) to afford 2-(4-(4-cyclohexylisoxazol-5-yl)phenyl)propan-2-ol as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 8.23 (s, 1H), 7.62 (m, 4H), 2.77 (m, 1H), 2.09 (m, 1H), 1.86 (m, 5H), 1.63 (s, 6H), 1.37 (m, 5H).

Provenance & Evidence