3-Butyn-2-ol → HCID 86680476, compound

To a stirred solution of 4-fluorobenzaldehyde oxime (0.2 g, 1.4 mmol) in DCM (10 mL) was added N-chlorosuccinamide (0.1 g, 1.4 mmol) and the reaction stirred for 1 hour at room temperature. But-3-yn-2-ol (0.23 g, 1.68 mmol) was added and the reaction mixture stirred at reflux for 3 h. After completion of the reaction (as monitored by TLC), the mixture was extracted with DCM (3×100 mL), the organic layer washed with water (100 mL) followed by brine (100 mL), dried over sodium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (60-120 mesh; using 50% ethyl acetate in hexanes) to obtain 1-(3-(4-fluorophenyl)isoxazol-5-yl)ethanol as liquid (0.15 g, 50% yield). 1H NMR (400 MHz, CDCl3): δ 7.76 (dd, 2H), 7.05 (t, 2H), 6.48 (s, 1H), 5.04 (q, 1H), 1.63 (d, 3H).

1. stirringthe reaction mixture stirred
2. temperatureat reflux for 3 h
3. customAfter completion of the reaction (as monitored by TLC)
4. extractionthe mixture was extracted with DCM (3×100 mL)
5. washthe organic layer washed with water (100 mL)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe crude product was purified by silica gel column chromatography (60-120 mesh; using 50% ethyl acetate in hexanes)

ORD record

ord-01a4987bddd2429d9173d23709d0c070

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809372B2