Ethyl acetate hexane → HCID 12071334, compound

HRID 2301968Notes

Reaction equation

HRID 2301968 reaction equation
C([O:3][C:4](=O)[C:5](=[CH:12][C:13]1[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:14]=1[N+:20]([O-])=O)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])C.CCOC(C)=O.CCCCCC>C(O)C.[Pd]>[CH2:10]([O:9][C:7](=[O:8])[CH2:6][CH:5]1[CH2:12][C:13]2[C:14](=[CH:15][CH:16]=[C:17]([OH:19])[CH:18]=2)[NH:20][C:4]1=[O:3])[CH3:11]

Participants

5

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 59038095HCID 59038095, compound

Product 1

HCID 12071334HCID 12071334, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(5-hydroxy-2-nitro-benzylidene)-succinic acid diethyl ester (3.8 g, 12 mmol) in ethanol (35 mL) was hydrogenated over 10% Pd—C (0.8 g) at 25° C. and 1 atm. After 20 h, the catalyst was filtered through diatomaceous earth and washed with ethanol (3×35 mL). The filtrate was concentrated giving a mixture of solid and foam (2.8 g). Flash chromatography (190 g silica; 20%, then 40% EtOAc-hexane) gives the title compound (1.3 g, 45% yield) as a pale yellow solid.

Workup

  1. filtrationthe catalyst was filtered through diatomaceous earth
  2. washwashed with ethanol (3×35 mL)
  3. concentrationThe filtrate was concentrated
  4. customgiving

Sources & evidence

ORD record
ord-e82dd523867e4244812d7bc99dd58bef
Source dataset
uspto-grants-2002_08
Patent number
US06429214B1

Reaction notes

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