Propargyl alcohol → [3-(4-Benzyloxy-phenyl)-isoxazol-5-yl]-methanol

2.27 g of 4-benzyloxy-benzaldehydeoxime (10 mmol; 92% purity) was dissolved in 40 ml of methylenechloride (0.25 M), and 1.77 ml of propargyl alcohol (30 mmol) was then added to the resulting solution. 13.7 ml of 10% NaOCl (20 mmol) was then dropwise added very slowly to the resulting solution by using a dropping funnel at 0° C. After the addition of NaOCl was completed, the resulting mixture was stirred for about 5 hours while the temperature was slowly raised to room temperature. Subsequently, the completion of the reaction was confirmed by liquid chromatography, the resultant was subjected to distillation under reduced pressure to evaporate methylenechloride therefrom, 200 ml of water was added to the residue, and the obtained solid was then filtered. The filtered compound was washed with a large amount of water, and then washed with diehtylether to obtain a solid compound. The obtained solid compound was purified with an ethylacetate/hexane solution (1:2) to obtain a white, solid [3-(4-benzyloxy-phenyl)-isoxazole-5-yl]-methanol(yield: 2.5 g).

1. customat 0° C
2. distillationthe resultant was subjected to distillation under reduced pressure
3. customto evaporate methylenechloride
4. addition200 ml of water was added to the residue
5. filtrationthe obtained solid was then filtered
6. washThe filtered compound was washed with a large amount of water
7. washwashed with diehtylether
8. customto obtain a solid compound
9. customThe obtained solid compound was purified with an ethylacetate/hexane solution (1:2)

ORD record

ord-f5b658c9a0f249c7a932c9a59a2f2b6d

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841335B2