Reacción #7930

Ecuación de reacción

4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

copper(I) cyanide

→

9a-butyl-4-cyano-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Rendimiento 81.0%

Disolventes

1-methyl-2-pyrrolidinone

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was partitioned between EtOAc (20 mL) and water (20 ml)
2. 2
   LavadoThe organic phase was washed with water (2×20 mL) and brine (10 mL)
3. 3
   Secadodried over MgSO4
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated under vacuum
6. 6
   OtroThe residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate

Procedimiento

A solution of 4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (50 mg, 0.138 mmol) in anhydrous 1-methyl-2-pyrrolidinone (0.276 mL) was treated with copper(I) cyanide (25 mg, 0.275 mmol). The resulting mixture was stirred under a nitrogen atmosphere and heated in an oil bath at 160° C. for 40 minutes. The mixture was partitioned between EtOAc (20 mL) and water (20 ml). The organic phase was washed with water (2×20 mL) and brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate, developing with 5% EtOAc in CH2Cl2, to afford 9a-butyl-4-cyano-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (33 mg) as an oil.

Fuente