Ethanol → 4-(4-(Hexyloxy)phenyl)thiophene-2-carboxylic acid

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Reaction Conditions

Reaction Steps

A mixture of silver nitrate (4.07 g, 24 mmol), compound 1026 (1.73 g, 6 mmol), ethanol (30 mL) and aqueous sodium hydroxide solution (1M, 48 mL) was stirred at 40° C. for 3 hours and then diluted with water (150 mL). The aqueous phase was washed with ethyl acetate (2×300 mL) and acidified to pH 1 with 1N aqueous hydrochloric acid solution. The aqueous solution was extracted with EtOAc (2×300 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated to yield compound 1027 (1.5 g) which was used directly in the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ 0.87 (m, 3H), 1.31-1.30 (m, 6H), 1.65 (m, 2H), 3.98 (m, 2H), 6.96 (d, J=8.4 Hz, 2H), 7.66 (d, J=8.7 Hz, 2H), 8.05 (s, 2H), 13.19 (s, 1H). MS m/z=303 [M−H]−.

Provenance & Evidence