Ethanol → HCID 70082202, compound

HRID 361380Notes

Reaction equation

HRID 361380 reaction equation
[C:1]([CH2:3][CH:4]1[CH:9]=[CH:8][CH:7]=[CH:6][O:5]1)#[N:2].C(O)C>[Pd].C(O)(=O)C>[NH2:2][CH2:1][CH2:3][CH:4]1[CH:9]=[CH:8][CH:7]=[CH:6][O:5]1

Participants

5

Reactant 2

HCID 702EthanolHCID 70081659HCID 70081659, compound

Product 1

HCID 70082202HCID 70082202, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of rac 2-cyanomethylpyran (4.2 g) and 10% Pd/C (4.0 g) in 1:1 ethanol:acetic acid (150 ml) was hydrogenated at 55 psi overnight. The reaction mixture was filtered through Celite and the solvents were then removed in vacuo. The residue was partitioned between chloroform and 10% sodium carbonate solution. The organic phase was dried over sodium sulfate. Removal of the solvent gave the title compound:

Workup

  1. customwas hydrogenated at 55 psi overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. customthe solvents were then removed in vacuo
  4. customThe residue was partitioned between chloroform and 10% sodium carbonate solution
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-84ba276d26244ecf89fb11bbaf301250
Source dataset
uspto-grants-1999_02
Patent number
US05866573

Reaction notes

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