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

HRID 78034Notes

Reaction equation

HRID 78034 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][CH:13]2[CH2:17][CH2:16][CH2:15][O:14]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 592551844-(2-(Tetrahydrofuran-2-yl)-ethyl)-benzoic acid ethyl esterYield 100%

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 (2.2 g, 9.39 mmol) described in Manufacturing Example 80-1-1 was added 10% palladium-carbon (50% hydrate, 1 g), which was stirred for 6 hours under hydrogen atmosphere at room temperature. The reaction liquid was filtered, and the filtrate was concentrated under a reduced pressure to obtain the title compound (2.2 g, 100%) as a crude product.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-1c64f16242ad40149e94ba70e1f85606
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

Loading…