Diisobutylaluminumhydride → (5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methanol

To a solution of ethyl 5-cyclopropyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate (289 mg, 0.886 mmol) in THF (4 mL) at 0° C. was slowly added diisobutylaluminum hydride (1.5M in toluene, 1.24 mL, 1.86 mmol). The solution was allowed to warm slowly to ambient temperature. After approximately 4 hours of stirring, the solution was re-cooled to 0° C. and an additional 1 mL of diisobutylaluminum hydride was added. After approximately 1.5 hours of stirring the mixture was re-cooled to 0° C., quenched with some aqueous Rochelle's salt and allowed to stir overnight while warming to ambient temperature. The mixture was extracted twice with ethyl acetate. The combined organic layers were washed once with Rochelle's Salt, dried over magnesium sulfate and concentrated to afford [5-cyclopropyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methanol (242 mg, 96%). 1H-NMR (400 MHz, DMSO-d6) δ 7.61-7.51 (m, 3H), 4.93 (t, J=5 Hz, 1H), 4.19 (d, J=5 Hz, 2H), 2.31-2.27 (m, 1H), 1.11-1.04 (m, 4H).

1. customat 0° C.
2. temperaturethe solution was re-cooled to 0° C.
3. stirringAfter approximately 1.5 hours of stirring the mixture
4. temperaturewas re-cooled to 0° C.
5. customquenched with some aqueous Rochelle's salt
6. stirringto stir overnight
7. temperaturewhile warming to ambient temperature
8. extractionThe mixture was extracted twice with ethyl acetate
9. washThe combined organic layers were washed once with Rochelle's Salt
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated

ORD record

ord-2b9f4476e8f44ab2b28122d950ce82a5

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960552B2