3-(4-Benzyloxy-benzofuran-7-yl)-2Z-ethoxy-acrylic acid ethyl ester → [rac]-2-Ethoxy-3-(4-hydroxy-2,3-dihydro-benzofuran-7-yl)-propionic acid ethyl ester

HRID 479203Notes

Reaction equation

HRID 479203 reaction equation
[CH2:1]([O:3][C:4](=[O:27])/[C:5](/[O:24][CH2:25][CH3:26])=[CH:6]/[C:7]1[C:15]2[O:14][CH:13]=[CH:12][C:11]=2[C:10]([O:16]CC2C=CC=CC=2)=[CH:9][CH:8]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:27])[CH:5]([O:24][CH2:25][CH3:26])[CH2:6][C:7]1[C:15]2[O:14][CH2:13][CH2:12][C:11]=2[C:10]([OH:16])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 686170643-(4-Benzyloxy-benzofuran-7-yl)-2Z-ethoxy-acrylic acid ethyl ester

Product 1

HCID 68617933[rac]-2-Ethoxy-3-(4-hydroxy-2,3-dihydro-benzofuran-7-yl)-propionic acid ethyl esterYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(4-benzyloxy-benzofuran-7-yl)-2Z-ethoxy-acrylic acid ethyl ester (420 mg, 1.15 mmol) (example 120 c]) in methanol (17 ml) was hydrogenated over 10% palladium on charcoal (100 mg) at ambient temperature for 20 h. The catalyst was filtered off, the solvent evaporated under reduced pressure and the residue chromatographed (silica gel, hexane/AcOEt=4/1) to give 240 mg (0.86 mmol, 75%) of the title compound as colorless liquid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated under reduced pressure
  3. customthe residue chromatographed (silica gel, hexane/AcOEt=4/1)

Sources & evidence

ORD record
ord-ebe415c872ec4050b60a5dc262462ed9
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

Loading…