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

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Reaction Steps

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.

Provenance & Evidence