4-((E)-2-furan-2-yl-vinyl)benzoic acid ethyl ester → 4-(2-Furan-2-yl-ethyl)-benzoic acid ethyl ester

HRID 78027Notes

Reaction equation

HRID 78027 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)=[CH:7][CH:6]=1)[CH3:2]>[C].[Pd].O1CCCC1>[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 1

HCID 592550674-((E)-2-furan-2-yl-vinyl)benzoic acid ethyl ester

Product 1

HCID 592551104-(2-Furan-2-yl-ethyl)-benzoic acid ethyl esterYield 65.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To an anhydrous tetrahydrofuran (25 mL) solution of 4-((E)-2-furan-2-yl-vinyl)-benzoic acid ethyl ester (1.07 g, 4.4 mmol) described in Manufacturing Example 80-1-1 was added 10% palladium-carbon (50% hydrate, 500 mg), which was added for 2 hours under a hydrogen atmosphere at room temperature. The reaction product was filtered, and the filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (t-butylmethyl ether: heptane=5:95) to obtain the title compound (706 mg, 65.4%).

Workup

  1. additionwas added for 2 hours under a hydrogen atmosphere at room temperature
  2. filtrationThe reaction product was filtered
  3. concentrationthe filtrate was concentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (t-butylmethyl ether: heptane=5:95)

Sources & evidence

ORD record
ord-879415cde28647bcbb44f517524588a4
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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