HCID 123554834, compound → 5-(Thiophen-3-yl)pentanoic acid

HRID 709394Notes

Reaction equation

HRID 709394 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=[CH:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:2]1.[H][H]>C(O)C>[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:2]1

Participants

4

Reactant 2

HCID 123554834HCID 123554834, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 247227355-(Thiophen-3-yl)pentanoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.3 g of the cis and trans mixture of 5-(thiophen-3-yl)-pent-4-enoic acid prepared in example 9a are solubilized in absolute ethanol (50 mL). The compound is then submitted to an hydrogenation reaction with hydrogen (3 atm of H2) on Pd/C 10% (180 mg) carried out at room temperature for a time of 18 hours. The reaction mixture is then filtered on celite and washed with methanol (3×10 mL). The solvent is removed under vacuum, obtaining 2.6 g of the 5-(thiophen-3-yl)-pentanoic acid (yield 80%). Rf=0.35 (ligroin/ethyl acetate 6/4 volume/volume); 1H NMR (CDCl3) δ (ppm): 8.35 (s, 1H, OH broad), 7.24 (m, 1H, ArH), 6.93 (m, 2H, ArH), 2.66 (m, 2H, CH2), 2.38 (m, 2H, CH2), 1.69 (m, 4H, CH2); 13C NMR (CDCl3) δ (ppm): 179.8, 142.3, 128.2, 125.3, 120.1, 33.9, 29.9, 24.4; FT-IR (film) νmax: 2944.3, 2865.4, 1692.9, 1462.7, 1425.3, 1307.6, 1258.2, 1212.9, 1190.2, 930.2, 750.8, 592.0 cm−1.

Workup

  1. customcarried out at room temperature for a time of 18 hours
  2. filtrationThe reaction mixture is then filtered on celite
  3. washwashed with methanol (3×10 mL)
  4. customThe solvent is removed under vacuum

Sources & evidence

ORD record
ord-58dbfa0e2f514a41958aac7602336578
Source dataset
uspto-grants-2015_11
Patent number
US09181196B2

Reaction notes

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