Propargyl alcohol → 3-(2-Pyridinyl)-5-isoxazolemethanol

Temperature

60 °C

A solution of (E)-picolinaldehyde oxime (4 g) in N,N-dimethylformamide (20 mL) was treated with N-chlorosuccinimide (4.81 g) at 0° C., in portions. The mixture was stirred at 60° C. for 2 hours. The mixture was then cooled to 0° C. and treated with prop-2-yn-1-ol (7.59 mL) through a syringe. A solution of triethylamine (5.02 mL) in N,N-dimethylformamide (4 mL) was added slowly (30 minutes). The resulting mixture was stirred at 0° C. for 1 hour, and then at room temperature for 18 hs. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate and water. The organic layer was separated, dried and evaporated in vacuo to a yellow oil and purified by column chromatography on silica gel (2-10% methanol in dichloromethane) to obtain the title compound (4.25 g) having the following physical data.

1. temperatureThe mixture was then cooled to 0° C.
2. stirringThe resulting mixture was stirred at 0° C. for 1 hour
3. customat room temperature
4. customThe solvent was evaporated in vacuo
5. customthe residue partitioned between ethyl acetate and water
6. customThe organic layer was separated
7. customdried
8. customevaporated in vacuo to a yellow oil
9. custompurified by column chromatography on silica gel (2-10% methanol in dichloromethane)

ORD record

ord-76e21045359b4a9793ff3508e4acb673

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809538B2