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 diethylether 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 diethylether
8. customto obtain a solid compound
9. customThe obtained solid compound was purified with an ethylacetate/hexane solution (1:2)

ORDレコード

ord-2dff27191cb34109a4d5e951e8089697

出典データセット

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09290464B2