Ethyl (2Z)-3-[4-(benzyloxy)-3-nitrophenyl]-2-ethoxyacrylate → HCID 22708431, compound

HRID 353304Notes

Reaction equation

HRID 353304 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[C:16](\[O:22][CH2:23][CH3:24])/[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][C:10]=1[N+:25]([O-])=O)C1C=CC=CC=1>C(OC(=O)C)C.[Pd]>[NH2:25][C:10]1[CH:11]=[C:12]([CH2:15][CH:16]([O:22][CH2:23][CH3:24])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

4

Reactant 1

HCID 86588959Ethyl (2Z)-3-[4-(benzyloxy)-3-nitrophenyl]-2-ethoxyacrylate

Product 1

HCID 22708431HCID 22708431, compoundYield 13.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl (2Z)-3-[4-(benzyloxy)-3-nitrophenyl]-2-ethoxyacrylate (0.83 g, 1.57 mmole) was hydrogenated in ethylacetate (10 ml) at atmospheric pressure using Pd/C (5%) as a catalyst. The mixture was filtered through celite and evaporated in vacuo. Purification of the crude product with preparative HPLC (Kromasil C8, 7 μm, 50×250 mm) using actonitrile(0-60%) in ammonium acetate buffer (pH 7) as mobile phase gave 0.052 g (13% yield) of the desired product.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated in vacuo
  3. customPurification of the crude product with preparative HPLC (Kromasil C8, 7 μm, 50×250 mm)

Sources & evidence

ORD record
ord-63e74a5376db4e6bb3c806db6a129c4a
Source dataset
uspto-grants-2004_06
Patent number
US06750252B2

Reaction notes

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