Sodium hydride → 5-benzyloxy-2-[3-(4-cyanophenoxy)-3-methyl-1-butenyl]pyridine N-oxide

HRID 1073943Notes

Reaction equation

HRID 1073943 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:16][CH:17](OS(C)(=O)=O)[C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)([CH3:20])[CH3:19])=[N+:13]([O-:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>C(O)(C)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:16]=[CH:17][C:18]([O:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]#[N:29])=[CH:26][CH:27]=2)([CH3:20])[CH3:19])=[N+:13]([O-:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 54352845HCID 54352845, compound

Product 1

HCID 543936855-benzyloxy-2-[3-(4-cyanophenoxy)-3-methyl-1-butenyl]pyridine N-oxideYield 121.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
20 °C

Procedure

1.69 g of 5-benzyloxy-2-[3-(4-cyanophenoxy)-3-methyl-2-(methylsulphonyloxy)butyl]pyridine N-oxide were added to a solution of 0.14 g of 80% sodium hydride in 15 ml of isopropanol and the solution was stirred at 20° C. for 16 hours. The solvent was then removed by evaporation and the residue was partitioned between ethyl acetate and sodium chloride solution The organic phase was washed with sodium chloride solution and then evaporated to give 1.64 g of 5-benzyloxy-2-[3-(4-cyanophenoxy)-3-methyl-1-butenyl]pyridine N-oxide in the form of a pale cream solid of melting point 125° C. after recrystallization from ethyl acetate.

Workup

  1. customThe solvent was then removed by evaporation
  2. customthe residue was partitioned between ethyl acetate and sodium chloride solution The organic phase
  3. washwas washed with sodium chloride solution
  4. customevaporated

Sources & evidence

ORD record
ord-01901d3d01a74a379136972f67d9cd0b
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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