HCID 13557760, compound → HCID 13557761, compound

HRID 1719835Notes

Reaction equation

HRID 1719835 reaction equation
[CH3:1][C:2]12[O:11][C:5]([CH3:12])([CH:6]([N+:8]([O-:10])=[O:9])[CH2:7]1)[CH:4]=[CH:3]2.[H][H]>C.[Pd].C(O)C>[CH3:12][C:5]12[O:11][C:2]([CH3:1])([CH2:3][CH2:4]1)[CH2:7][CH:6]2[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 2

HCID 13557760HCID 13557760, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 13557761HCID 13557761, compoundYield 86.2%

Reagents, catalysts & solvents 3

HCID 297MethaneCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5.5 g of 1,4-dimethyl-5-nitro-7-oxabicyclo[2.2.1]hept-2-ene was placed in a 1/2 liter Parr bomb with 50 ml of ethanol and 10% palladium on powdered charcoal catalyst. The bomb was charged with hydrogen gas under 50 lb pressure. After using 3 lb of hydrogen gas, the reaction mixture was removed from the bomb, filtered to remove the catalyst, and stripped. The residue taken up in ether, was washed with water, dried (MgSO4), filtered and stripped to yield 4.8 g of the desired product as a brownish oil.

Workup

  1. customthe reaction mixture was removed from the bomb
  2. filtrationfiltered
  3. customto remove the catalyst
  4. washwas washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-c3ae1c3573914b1db8676a4b055fa950
Source dataset
uspto-grants-1985_09
Patent number
US04542244

Reaction notes

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