Sodium hydride → HCID 53754707, compound

HRID 892550Notes

Reaction equation

HRID 892550 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]([CH3:25])([CH3:24])[CH:9](OS(C)(=O)=O)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N+:12]=2[O-:18])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+]>C(O)(C)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]([CH3:24])([CH3:25])[CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N+:12]=2[O-:18])=[CH:26][CH:27]=1)#[N:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86744355HCID 86744355, compound

Product 1

HCID 53754707HCID 53754707, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.7 g of 2-[3-(4-cyanophenoxy)-2-methanesulphonyloxy-3-methylbutyl]-6-methylpyridine N-oxide were added to a solution of 200 mg of 80% sodium hydride in 25 ml of isopropanol and the mixture was stirred for 30 minutes. The solvent was removed by evaporation and the residue was partitioned between water and dichloromethane. The organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using 10% (v/v) methanol/ethyl acetate for the elution. There were obtained 960 mg of 2-[3-(4-cyanophenoxy)-3-methyl-1butenyl]-6-methylpyridine N-oxide as a colourless gum.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was partitioned between water and dichloromethane
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel using 10% (v/v) methanol/ethyl acetate for the elution

Sources & evidence

ORD record
ord-ab426d9d3d5341079df8c8582ced1131
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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