Water → HCID 18463960, compound

Participants

Reaction Steps

To a solution of 5-(3-[1,3-dioxolan-2-yl]propyl)-2-thiophene carboxylic acid (58.0 g, 239 mmol) in 300 mL of dimethylformamide was added potassium carbonate (41.4 g, 299 mmol) followed by methyl iodide (51.0 g, 359 mmol). The slurry was stirred at ambient temperature for 17 hours and then poured into 600 mL of water. The resulting suspension was extracted twice with 500 mL of t-butylmethylether and the combined extracts were washed with water, dried over magnesium sulfate, filtered, and concentrated by rotory evaporation to afford 57.84 g (94.3%) of the title compound which was of sufficient purity for use in Preparation 3. IR (CHCl3, cm−1) 3021, 1707, 1541, 1463, 1296, 1101. 1H NMR (300 MHz, CDCl3) d 1.75 (m, 4H), 2.84 (t, J=7.4 Hz, 2H), 3.81 (s, 3H), 3.82 (m, 2H), 3.92 (m, 2H), 4.84 (t, J=4.3 Hz, 1H), 6.76 (d, J=3.9 Hz, 1H), 7.58 (d, J=3.7 Hz, 1H).

Provenance & Evidence