Reacción #2336522

Ecuación de reacción

Toluenesulfonyl chloride

7-furyl-3-methyl-4-chromanone oxime

pyridine

→

7-furyl-3-methyl-4-chromanone O-(toluenesulfonyl)-oxime

Rendimiento 57.1%

Disolventes

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with 5% HCl (20 mL)
2. 2
   SecadoThe organic layer was dried over MgSO4
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe residue was purified via flash chromatography

Procedimiento

Toluenesulfonyl chloride (397 mg, 2.08 mmol) was added to a 0° C. solution of 7-furyl-3-methyl-4-chromanone oxime (61) (461 mg, 1.89 mmol) and pyridine (0.5 mL) in CH2Cl2 (10 mL). After 6 hours, the mixture was diluted with CH2Cl2 (30 mL) and washed with 5% HCl (20 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified via flash chromatography using 5:1 hexanes:EtOAc as the eluent, to provide 7-furyl-3-methyl-4-chromanone O-(toluenesulfonyl)-oxime (62) (429 mg) as a pink solid, m.p. 163-164° C. (dec).

Fuente