Sodium hydride → 3-Cyclopropyl-3-oxo-2-[(2'-nitrobiphen-4-yl)methyl]propanenitrile

HRID 257255

Reaction equation

HRID 257255 reaction equation
[CH:1]1([C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])=[CH:15][CH:14]=1>CS(C)=O.[Cl-].[Na+].O>[CH:1]1([C:4](=[O:8])[CH:5]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N+:25]([O-:27])=[O:26])=[CH:17][CH:18]=2)[C:6]#[N:7])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 98127633-Cyclopropyl-3-oxopropanenitrileHCID 117790721,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-

Product 1

HCID 1317181973-Cyclopropyl-3-oxo-2-[(2'-nitrobiphen-4-yl)methyl]propanenitrileYield 34%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2.61 g (24.0 mmol) 3-cyclopropyl-3-oxopropanenitrile in 150 mL DMSO was added 1.01 g (25.2 mmol) 60% NaH in oil. After 1 hour, 3.50 g (12.0 mmol) 4'-bromomethyl-2-nitrobiphenyl was added all at once to the solution. After 3 hours, the solution was poured into brine and extracted 3 times with ether. The combined organic material was dried over MgSO4, stripped of solvent in vacuo, and was chromatographed on silica gel under medium pressure using 3/40/57 EtOAc/CH2Cl2/hexanes to give 1.29 g (34% yield) of the title compound as a yellow glass. Rf 0.13 in 3/40/57 EtOAc/CH2Cl2/hexanes, visualized by UV and ammonium molybdate/ceric sulfate stain; Rf of the dialkylated material is 0.19 in the same solvent mixture.

Workup

  1. waitAfter 3 hours
  2. extractionextracted 3 times with ether
  3. dry with materialThe combined organic material was dried over MgSO4
  4. customwas chromatographed on silica gel under medium pressure

Sources & evidence

ORD record
ord-50371f6999eb4c8eacd07d7b1e8acde9
Source dataset
uspto-grants-1993_11
Patent number
US05260285

Linked notes

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