Methanol → HCID 4979911, compound

Temperature

-78 °C

To a mixture of 5-(2-methoxyphenyl)-3-(trifluoromethyl)-1,2-oxazole (C10) (502 mg, 2.06 mmol) and tetra-n-butylammonium iodide (915 mg, 2.48 mmol) in dichloromethane (20 mL) cooled to −78° C. was added boron trichloride (1 M in dichloromethane, 4.95 mL, 4.95 mmol). The reaction was allowed to stir at room temperature for 24 hours, and then cooled to −78° C., whereupon methanol (3 mL) was slowly added followed by water (30 mL). The mixture was extracted with dichloromethane (2×10 mL), and the combined organic layers were dried over sodium sulfate and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 20% tert-butyl methyl ether in heptanes) afforded the title compound as a white solid. Yield: 283 mg, 1.23 mmol, 60%. 1H NMR (400 MHz, CDCl3) δ 5.94 (s, 1H), 6.96 (br d, J=8.2 Hz, 1H), 7.02 (s, 1H), 7.09 (br dd, J=8, 8 Hz, 1H), 7.39 (ddd, J=8, 8, 1.6 Hz, 1H), 7.89 (dd, J=7.9, 1.7 Hz, 1H).

1. additionwas slowly added
2. extractionThe mixture was extracted with dichloromethane (2×10 mL)
3. dry with materialthe combined organic layers were dried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customPurification via silica gel chromatography (Gradient: 0% to 20% tert-butyl methyl ether in heptanes)

ORD record

ord-db99a89a8e23470781b9d452cf97dbc1

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067934B2