HCID 58541880, compound → HCID 58541915, compound

To a solution of (2-isoxazol-5-yl-phenyl)-methanol (170 mg, 0.97 mmol) in THF (9 mL) is added manganese dioxide (1.29 g, 14.55 mmol). The reaction mixture is stirred at room temperature for 18 hours. After this time, the reaction mixture is filtered through celite and the filtrate is concentrated in vacuo and is redissolved in THF (11 mL) and more manganese dioxide (1.07 g, 10.46 mmol) is added. The reaction mixture is stirred at room temperature for 65 hours. After this time, the reaction mixture is filtered through celite and the celite is washed with EtOAc (20 mL). The filtrate is concentrated in vacuo and the residue is purified using silica gel flash column chromatography with 20-100% EtOAc in heptane as the eluent to give 2-isoxazol-5-yl-benzaldehyde (50 mg, 30%).

1. filtrationAfter this time, the reaction mixture is filtered through celite
2. concentrationthe filtrate is concentrated in vacuo
3. dissolutionis redissolved in THF (11 mL)
4. stirringThe reaction mixture is stirred at room temperature for 65 hours
5. filtrationAfter this time, the reaction mixture is filtered through celite
6. washthe celite is washed with EtOAc (20 mL)
7. concentrationThe filtrate is concentrated in vacuo
8. customthe residue is purified

ORD record

ord-92068dc6d25e4be2bf1183aa00095103

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420655B2