Norbornadiene → 3-(4-Nitrophenyl)isoxazole

HRID 1371826Notes

Reaction equation

HRID 1371826 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH:8]=[N:9][OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:13]12CC(C=C1)C=[CH:14]2.[O-]Cl.[Na+]>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]2[CH:14]=[CH:13][O:10][N:9]=2)=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8473NorbornadieneHCID 96339p-Nitrobenzaldoxime2×HCID 23665760Sodium Hypochlorite

Product 1

HCID 6054383-(4-Nitrophenyl)isoxazoleYield 43.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

4-Nitrobenzaldehyde oxime (Intermediate 3, 20 g, 120.5 mmol) and bicyclo[2.2.1]hepta-2,5-diene (32.45 ml, 3015.25 mmol) were added to THF (200 ml) followed by dropwise addition of bleach (6.15% NaOCl, 861.5 ml). The reaction was allowed to stir overnight and then the THF and H2O layers were separated, the THF layer was dried over Na2SO4 and then concentrated under vacuum. The dried material was added to dioxane and heated to 100° C. for 7 days. The crude material was purified by column chromatography using 5–50% EtOAc in hexanes to yield the final product (10 g).

Workup

  1. customthe THF and H2O layers were separated
  2. dry with materialthe THF layer was dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. additionThe dried material was added to dioxane
  5. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-dfe263e0e5194a4caa2b733823c2bab9
Source dataset
uspto-grants-2007_01
Patent number
US07157482B2

Reaction notes

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