Ethanol → HCID 10571122, compound

HRID 725031Notes

Reaction equation

HRID 725031 reaction equation
[CH2:1]([O:3][C:4]([CH:6]=[CH:7][C:8]1[CH:9]=[C:10]([CH:18]=[C:19]([CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:20]=1)[CH:11]=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:5])[CH3:2].C([O-])=O.[NH4+].C(O)C>[Pd].O1CCCC1>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:18]=[C:19]([CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:20]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 53881501HCID 53881501, compound

Product 1

HCID 10571122HCID 10571122, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

10% Palladium on charcoal catalyst (1.30 g) was added portionwise to a stirred mixture of ethyl 3-(2-ethoxycarbonyl-1-ethenyl)-5-(3-pyridylmethyl)cinnamate Preparation 13; 13.0 g), ammonium formate (22.44 g), ethanol (100 ml) and tetrahydrofuran (100 ml) at room temperature under an atmosphere of dry nitrogen. The mixture was heated at 60° C. for 2 hours, then cooled and filtered. The filtrate was evaporated under vacuum and the residue partitioned between dichloromethane and water. The aqueous layer was separated and extracted with dichloromethane. The organic solutions were combined, dried (MgSO4) and evaporated under vacuum to give the title compound as an oil (12.46 g); Rf 0.40 (SS 1); δ (CDCl3): 1.20(6H,t,J=7.1 Hz), 2.55(4H,t,J=7.8 Hz), 2.86(4H,t,J=7.8 Hz), 3.89(2H,s), 4.09(4H,q,J=7.1 Hz), 6.84(2H,s), 6.89(1H,s), 7.16-7.20(1H,m), 7.41-7.45(1H,m), 8.43-8.47(1H,m).

Workup

  1. customat room temperature
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated under vacuum
  5. customthe residue partitioned between dichloromethane and water
  6. customThe aqueous layer was separated
  7. extractionextracted with dichloromethane
  8. dry with materialdried (MgSO4)
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-f011a0946911420dbb975b036cc4a974
Source dataset
uspto-grants-1998_01
Patent number
US05705523

Reaction notes

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