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

4-benzyloxy-benzaldehyde oxime (2.27 g, 10 mmol-a compound of 92% purity) was dissolved in methylene chloride (40 ml, 0.25 M), to which solution was added propargyl alcohol (1.77 ml, 30 mmol). To the resulting solution was very slowly dropwise added 10% NaOCl (13.7 ml, 20 mmol) at 0° C., 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 the mixture was distilled under reduced pressure to remove the 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 2.50 g of [3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methanol as a white solid.

1. customat 0° C.
2. distillationthe mixture was distilled under reduced pressure
3. customto remove the methylene chloride
4. additionWater (200 ml) was added to the residue
5. filtrationthe resulting solid was filtered off
6. washThe filtered compound was washed with excess of water
7. washfinally washed with diethyl ether
8. customThe thus-obtained solid compound was recrystallized from ethyl acetate/hexane (1:2)

ORD record

ord-5fbbabaf954345bd939643f966166217

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828992B2