HCID 53633682, compound → HCID 53647404, compound

HRID 1779329Notes

Reaction equation

HRID 1779329 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20])[C:17]#[N:18])[CH:8]=[CH:9][C:10]=1[O:11][C:12](=[O:14])[CH3:13])(=[O:3])[CH3:2].[H][H]>C(OC(=O)C)(=O)C.[Pd]>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:15][CH:16]([P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20])[C:17]#[N:18])[CH:8]=[CH:9][C:10]=1[O:11][C:12](=[O:14])[CH3:13])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 53633682HCID 53633682, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53647404HCID 53647404, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

3-(3,4-Diacetoxyphenyl)-2-(diethoxyphosphinyl) acrylonitrile (Table 1, No. 56; 2.5 g; 0.0066 mol) was hydrogenated in 100 ml of acetic anhydride over 0.5 g of 10 percent Pd/C catalyst in a Parr hydrogenation apparatus under an initial pressure of 3.45 bar until hydrogen uptake was complete (16 hours), adding an additional 0.3 g of catalyst after 8 hours had elapsed. Finally, the catalyst was filtered off and the filtrate was evaporated under reduced pressure. The residue was chromatographed on silica gel, eluted with the solvent mixture dichloromethane:ethyl acetate (7:3). This results in the title compound as a pale oil in a yield of 1.7 g (67.7% of theory).

Workup

  1. custom(16 hours)
  2. filtrationFinally, the catalyst was filtered off
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was chromatographed on silica gel
  5. washeluted with the solvent mixture dichloromethane:ethyl acetate (7:3)

Sources & evidence

ORD record
ord-ad9de76693e242618ac1f457a08391e5
Source dataset
uspto-grants-1997_05
Patent number
US05627173

Reaction notes

Loading…