HCID 58043931, compound → 3-(1-Benzothiophen-3-yl)propanoic acid

HRID 1919128Notes

Reaction equation

HRID 1919128 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](/[CH:10]=[CH:11]\[C:12]([OH:14])=[O:13])=[CH:2]1>[Pd].CO.C(OCC)(=O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:2]1

Participants

4

Reactant 1

HCID 58043931HCID 58043931, compound

Product 1

HCID 123189833-(1-Benzothiophen-3-yl)propanoic acidYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A suspension of 329a (5.5 g, 27 mmol) and 10% Pd/C (600 mg) in 1:1 methanol/ethyl acetate (100 mL) was hydrogenated in a Parr apparatus at 50 psi for overnight. The mixture was filtered through a pad of Celite and the filtrate was concentrated under reduced pressure to give crude 329b as a brown solid (5.0 g, 90%), which was used without further purification for the next step. MS: [M+H]+ 207. 1H NMR (500 MHz, CDCl3) δ 2.81-2.84 (t, J=8.5, 2H), 3.18-3.21 (m, 2H), 7.16 (s, 1H), 7.34-7.41 (m, 2H), 7.74-7.76 (d, 1H), 7.85-7.87 (d, 1H).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d3ffbc8ca1024daebe4fb8e8c244c6f3
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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