1,4-Dioxane → HCID 18322386, compound

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Reaction Steps

Allyl 3-(N-carbo-tert-butoxyamino)-5-tert-butylthiophene-2-carboxylate (0.14 g, 0.41 mmol) was dissolved in solution of HCl in dioxane (4N, 11.0 mL, 4.1 mmol, 10 equiv). The resulting solution was stirred at room temp. for 5 d, diluted with CHCl, (5 mL), washed with a 1N HCl solution (5 mL) and a saturated NaCl solution (5 mL), dried Na2SO4), and concentrated under reduced pressure. The residue was filtered through a plug of SiO2 with the aid of a 10% EtOAc/CH2Cl2 solution to give allyl 3-amino-5-tert-butylthiophene-2-carboxylate as a yellow oil (0.088 g, 95%): 1H NMR (CDCl3) δ1.32 (s, 9H), 4.72 (ddd, J=4.1, 1.5, 1.5 Hz, 2H), 5.21 (ddd, J=10.3, 2.9, 1.5 Hz, 1H), 5.36 (ddd, J=17.3, 3.1, 1.5, 1H), 5.42 (br s, 2H), 5.92-6.03 (m, 1H), 6.34 (s, 1H). This material was used without further purification.

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