7-Oxabicyclo[2.2.1]hept-5-ene-2-carbonitrile → 89937-59-7

HRID 626527Notes

Reaction equation

HRID 626527 reaction equation
[CH:1]12[O:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]#[N:9]>CCOC(C)=O.[Pd]>[CH:1]12[O:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:8]#[N:9]

Participants

4

Reactant 1

HCID 122210077-Oxabicyclo[2.2.1]hept-5-ene-2-carbonitrile

Product 1

HCID 1228208889937-59-7Yield 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

The exo/endo-mixture of 7-oxabicyclo[2.2.1]hept-5-ene-2-carbonitrile (4.70 g, 38.8 mmol) in EtOAc (30 mL) was dissolved in EtOAc (30 mL), treated with 10% Pd/C (0.300 g, 0.282 mmol) and hydrogenated (20 psi) for 2 h. The solids were removed via filtration, washed with EtOAc and the filtrate concentrated in vacuo to afford an exo/endo-mixture of 7-oxabicyclo[2.2.1]heptane-2-carbonitrile (4.80 g, 100%) as a colorless oil.

Workup

  1. customThe solids were removed via filtration
  2. washwashed with EtOAc
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-2324b1575e0e456cbd081320d37e941d
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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