(E)-3-(3-Chloro-benzo[b]thiophen-2-yl)-acrylic acid methyl ester → 3-(3-Chloro-benzo[b]thiophen-2-yl)-propionic acid methyl ester

HRID 1749226Notes

Reaction equation

HRID 1749226 reaction equation
[CH3:1][O:2][C:3](=[O:16])/[CH:4]=[CH:5]/[C:6]1[S:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[C:7]=1[Cl:15]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[S:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[C:7]=1[Cl:15]

Participants

4

Reactant 1

HCID 46825722(E)-3-(3-Chloro-benzo[b]thiophen-2-yl)-acrylic acid methyl ester

Product 1

HCID 667607513-(3-Chloro-benzo[b]thiophen-2-yl)-propionic acid methyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.60 g (14.6 mmol) of 14 in 50 mL THF was treated with Wilkinson's catalyst (3.35 g, 3.62 mmol). The mixture was stirred under 1 atm H2 for 18 h and then was filtered through celite. The solvent was evaporated and the residue purified by flash chromatography on silica gel (0-2% ethyl acetate/hexane) to give 3.63 g (14.3 mmol, 99%) of the saturated ester (15).

Workup

  1. filtrationwas filtered through celite
  2. customThe solvent was evaporated
  3. customthe residue purified by flash chromatography on silica gel (0-2% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c53e429a6d58495bb9203660e1ec6862
Source dataset
uspto-grants-2015_10
Patent number
US09156810B2

Reaction notes

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