Phenylacetonitrile → 4-nitro-alpha-phenyl-3-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]benzeneacetonitrile

Participants

Reaction Steps

To a mixture of 7.13 parts of a dispersion of sodium hydride in mineral oil (50%) and 94 parts of N,N-dimethylacetamide was added dropwise a solution of 9.1 parts of benzeneacetonitrile in 18.8 parts of N,N-dimethylacetamide. After the hydrogen evolution had ceased, there were added 1.28 parts of tris-2,2,2-(2-methoxyethoxy)ethanamine and a solution of 20.2 parts of intermediate 54, namely 2-[(5-chloro-2-nitrophenyl)methoxy]-tetrahydro-2H-pyran, in 28.2 parts of N,N-dimethylacetamide. After 15 minutes, the reaction mixture was poured into ice-water and the whole was neutralized. The product was extracted with dichloromethane and the extract was dried, filtered and evaporated, yielding 26.2 parts (100%) of 4-nitro-α-phenyl-3-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]benzeneacetonitrile (interm. 55).

Provenance & Evidence