5-benzyloxy-2-[3-(4-cyanophenoxy)-3-methyl-1-butenyl]pyridine N-oxide → 5-benzyloxy-2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide

HRID 892574Notes

Reaction equation

HRID 892574 reaction equation
[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: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>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:16]2[C:27]3[CH:26]=[C:25]([C:28]#[N:29])[CH:24]=[CH:23][C:22]=3[O:21][C:18]([CH3:20])([CH3:19])[CH2:17]2)=[N+:13]([O-:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

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

Product 1

HCID 538667995-benzyloxy-2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxideYield 20.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.24 g of 5-benzyloxy-2-[3-(4-cyanophenoxy)-3-methyl-1-butenyl]pyridine N-oxide in 45 ml of toluene were heated to 80° C. for 12 hours. The solvent was removed by evaporation and the residue was chromatographed on silica gel using diethyl ether/methanol (97.5:2.5) for the elution to give 0.45 g of 5-benzyloxy-2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide in the form of a white solid of melting point 224° C.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was chromatographed on silica gel
  3. washfor the elution

Sources & evidence

ORD record
ord-f24bae491d9b42d7bf172d0f71f0c058
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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