Sodium hydride → HCID 20535520, compound

HRID 1156211Notes

Reaction equation

HRID 1156211 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][OH:10])=[CH:6][CH:5]=1.Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1>CS(C)=O>[CH3:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][O:10][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridineHCID 952944-Methylphenethyl alcohol

Product 1

HCID 20535520HCID 20535520, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of sodium hydride (60% oily suspension) (8.0 g) in 200 ml of dimethylsulfoxide was added dropwise 27.2 g of p-methylphenethyl alcohol at a temperature below 20° C. under ice-cooling, followed by stirring at room temperature for 1 hour. To the resultant mixture, was added dropwise a solution of 31.7 g of 2-chloro-5-nitropyridine in 100 ml of dimethylsulfoxide, and the resulting mixture was heated at 60° C. for 1 hour. After cooling, the reaction mixture was poured into ice water and extracted with ethyl acetate. The extracts were washed with water and dried over magnesium sulfate. After removal of the solvent, the oily products were purified by column chromatography on silica gel using benzene as an eluent to give 28.9 g of 2-(4-methylphenethyloxy)-5-nitropyridine as yellow crystals. Yield, 56%. M.P., 85°-85.5° C.

Workup

  1. temperaturecooling
  2. temperaturethe resulting mixture was heated at 60° C. for 1 hour
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with water
  6. dry with materialdried over magnesium sulfate
  7. customAfter removal of the solvent
  8. customthe oily products were purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9994bb608c38420c8b268f7b18c57520
Source dataset
uspto-grants-1982_06
Patent number
US04334912

Reaction notes

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