Methyl 5-Acetoxy-2-formyl-4-methoxycinnamate → Methyl 5-Acetoxy-2-formyl-4-methoxyhydrocinnamate

HRID 1898761Notes

Reaction equation

HRID 1898761 reaction equation
[C:1]([O:4][C:5]1[C:6]([O:19][CH3:20])=[CH:7][C:8]([CH:17]=[O:18])=[C:9]([CH:16]=1)[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[O:13])(=[O:3])[CH3:2]>[Pd].C(OCC)(=O)C>[C:1]([O:4][C:5]1[C:6]([O:19][CH3:20])=[CH:7][C:8]([CH:17]=[O:18])=[C:9]([CH:16]=1)[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 53756943Methyl 5-Acetoxy-2-formyl-4-methoxycinnamate

Product 1

HCID 23372351Methyl 5-Acetoxy-2-formyl-4-methoxyhydrocinnamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 5-acetoxy-2-formyl-4-methoxycinnamate (10.8 g) and 10% palladium on carbon (3 g) in ethyl acetate (100 ml) is hydrogenated at 45 psi for about 18 hours and filtered. The filtrate is concentrated in vacuo and the residue purified by HPLC, eluting 50% ethyl acetate in hexanes, to give the desired product.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated in vacuo
  3. customthe residue purified by HPLC
  4. washeluting 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d02b5e2cb1c64e93bd705cc8158c50d1
Source dataset
uspto-grants-1996_11
Patent number
US05571506

Reaction notes

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