Ethanol → 3a,4,4a,7a,8,8a-Hexahydro-3-methyl-4,8-methanofuro-[3,4-f]-1,2-benzisoxazole-5,7-dione

HRID 344789Notes

Reaction equation

HRID 344789 reaction equation
[CH2:1]1[C@@H:5]2[CH:6]3[C:11](=[O:12])[O:10][C:8](=[O:9])[CH:7]3[C@H:2]1[CH:3]=[CH:4]2.C1(N=C=O)C=CC=CC=1.[N+:22]([CH2:25][CH3:26])([O-])=[O:23].C(O)C>O1CCCC1.C(N(CC)CC)C>[CH3:26][C:25]1[CH:4]2[CH:5]3[CH2:1][CH:2]([CH:3]2[O:23][N:22]=1)[CH:7]1[C:8](=[O:9])[O:10][C:11](=[O:12])[CH:6]31

Participants

7

Reactant 4

HCID 702EthanolHCID 6587NitroethaneHCID 7672Phenyl isocyanateHCID 9964188cis-5-Norbornene-endo-2,3-dicarboxylic anhydride

Product 1

HCID 150082773a,4,4a,7a,8,8a-Hexahydro-3-methyl-4,8-methanofuro-[3,4-f]-1,2-benzisoxazole-5,7-dione

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4.0 g (24.4 mmol) of cis-5-norbornene-endo-2,3-dicarboxylic anhydride and 5.8 g (48.8 g) of phenyl isocyanate in 20 ml of tetrahydrofuran is treated dropwise with a solution of 1.83 g (1.76 ml, 24.4 mmol) of nitroethane and 6 drops of triethylamine in 10 ml of tetrahydrofuran. The mixture is maintained with stirring for 1 hour. The reaction mixture is filtered and the filtrate evaporated. Trituration with ethyl ether, filtration and drying gives 3.97 g of crude product. Trituration with 100 ml of ethanol (2 times) gives after filtration and drying 2.28 g of the title compound: m.p. 194°-197° C.

Workup

  1. temperatureThe mixture is maintained
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate evaporated
  4. filtrationTrituration with ethyl ether, filtration
  5. customdrying
  6. customgives 3.97 g of crude product
  7. filtrationafter filtration
  8. dry with materialdrying 2.28 g of the title compound

Sources & evidence

ORD record
ord-7581525ba8ec4bbb986455c4bb0641c7
Source dataset
uspto-grants-1991_10
Patent number
US05053508

Reaction notes

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