Reacción #43640

Ecuación de reacción

7-bromo-2,3-dihydro-1-benzofuran-5-carbaldehyde

copper(I) cyanide

→

desired product

Rendimiento 61.4%

5-formyl-2,3-dihydro-1-benzofuran-7-carbonitrile

Rendimiento 61.4%

Disolventes

dimethylacetamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was refluxed for 18 hours
2. 2
   Concentraciónconcentrated under reduced pressure
3. 3
   LavadoThe residue was washed well with warm ethyl acetate
4. 4
   ConcentraciónThe combined ethyl acetate layer were concentrated
5. 5
   Otrodried
6. 6
   OtroThe crude product was purified by flash column chromatography (silica gel, 4:1 and 2:1 hexane:ethyl acetate gradient)

Procedimiento

To a solution of 7-bromo-2,3-dihydro-1-benzofuran-5-carbaldehyde (1.3 g, 4.7 mmol) in dimethylacetamide (2 mL) was added copper(I) cyanide (0.41 g g, 4.7 mmol). The reaction was refluxed for 18 hours, and then concentrated under reduced pressure. The residue was washed well with warm ethyl acetate. The combined ethyl acetate layer were concentrated and dried. The crude product was purified by flash column chromatography (silica gel, 4:1 and 2:1 hexane:ethyl acetate gradient) to afford the desired product (0.5 g, 50%).

Fuente