Propargyl alcohol → [3-(4-Nitro-phenyl)-isoxazol-5-YL]-methanol

4-nitro-benzaldehyde oxime (2.40 g, 14.4 mmol) was dissolved in methylene chloride (70 ml, 0.2 M), and then propargyl alcohol (2.51 ml, 43.2 mmol) was added to the solution. To the resulting solution was slowly added dropwise 10% NaOCl (17.8 ml, 28.8 mmol) using a dropping funnel. After the addition of NaOCl was completed, the mixture was stirred for about 5 hours while increasing the temperature slowly to room temperature. The completion of the reaction was confirmed by liquid chromatography, and then the mixture was distilled under reduced pressure to remove methylene chloride. Water (200 ml) was added to the residue and the resulting solid was filtered off. The filtered compound was washed with excess of water and finally washed with diethyl ether. The thus-obtained solid compound was recrystallized from ethyl acetate/hexane (1:2) to obtain [3-(4-nitro-phenyl)-isoxazol-5-yl]-methanol in a white sold phase.

1. distillationthe mixture was distilled under reduced pressure
2. customto remove methylene chloride
3. additionWater (200 ml) was added to the residue
4. filtrationthe resulting solid was filtered off
5. washThe filtered compound was washed with excess of water
6. washfinally washed with diethyl ether
7. customThe thus-obtained solid compound was recrystallized from ethyl acetate/hexane (1:2)

ORD record

ord-bc9f7ab6e6584dfc9e753fab4cd1fdfb

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828992B2