HCID 69886837, compound → 3-(2-Bromo-thiophen-3-yl)-propionic acid ethyl ester

HRID 2084352Notes

Reaction equation

HRID 2084352 reaction equation
[CH2:1]([O:3][C:4](=[O:13])/[CH:5]=[CH:6]/[C:7]1[CH:11]=[CH:10][S:9][C:8]=1[Br:12])[CH3:2]>C(O)C>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH2:6][C:7]1[CH:11]=[CH:10][S:9][C:8]=1[Br:12])[CH3:2]

Participants

3

Reactant 1

HCID 69886837HCID 69886837, compound

Product 1

HCID 698883563-(2-Bromo-thiophen-3-yl)-propionic acid ethyl esterYield 85.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the ester of Example 23(d) (5.217 g, 20.0 mmol) and (PPh3)3RhCl (1.56 g, 1.69 mmol, Aldrich) in ethanol (60 mL) was stirred under a balloon of H2 for 23 h. The mixture was then filtered through celite and evaporated. The residue was purified by flash chromatography (5% ethyl acetate/hexanes→10%) to give 3-(2-Bromo-thiophen-3-yl)-propionic acid ethyl ester (4.507 g, 17.1 mmol, 85%).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. customevaporated
  3. customThe residue was purified by flash chromatography (5% ethyl acetate/hexanes→10%)

Sources & evidence

ORD record
ord-59ff61973cee4f68bb5986cb317b3103
Source dataset
uspto-grants-2004_04
Patent number
US06716864B2

Reaction notes

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