Toluene → [3-{[(2,6-Dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methanol

Participants

Reaction Steps

To a solution of methyl 3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolecarboxylate (50 mg, 0.14 mmol) in tetrahydrofuran (0.5 mL) at 0° C. was slowly added a 1.5 M solution of diisobutylaluminum hydride in toluene (0.46 mL, 0.69 mmol). The solution was allowed to warm slowly to ambient temperature and stir overnight. The next day the solution was cooled to 0° C. and methanol (approximately 0.25 mL) was added followed by aqueous Rochelle's salt (approximately 3 mL). The mixture was diluted with ethyl acetate and allowed to warm to ambient temperature while stirring. The layers were separated and the organic layer was dried over magnesium sulfate and concentrated to afford [3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methanol (43 mg, 93%). 1H-NMR (400 MHz, CDCl3) δ 7.35-7.16 (m, 3H), 4.60 (s, 2H), 4.10 (s, 2H), 3.17 (septet, J=8 Hz, 1H), 1.28 (d, J=6 Hz, 6H).

Provenance & Evidence