Phenylacetonitrile → 4-nitro-alpha-phenyl-3-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]benzeneacetonitrile
Reaction equation
[H-].[Na+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H].Cl[C:15]1[CH:16]=[CH:17][C:18]([N+:29]([O-:31])=[O:30])=[C:19]([CH2:21][O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH:20]=1>CN(C)C(=O)C>[N+:29]([C:18]1[CH:17]=[CH:16][C:15]([CH:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:10]#[N:11])=[CH:20][C:19]=1[CH2:21][O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)([O-:31])=[O:30]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
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).
Workup
- extractionThe product was extracted with dichloromethane
- customthe extract was dried
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-f0025e0924324bb4ad8ce694b616083a
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05037829
Reaction notes
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