3-Methyl-2-butenoic acid → 3-Azido-3-methylbutanoic acid

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Reaction Steps

According to the method of S, Nagarajan and B. Ganem, J. Org. Chem., 51, 4856, (1986), sodium azide (52 g, 0.8 mol) in water (100 mL) was added to a stirred solution of 3,3-dimethylacrylic acid (20 g, 0.2 mol) in glacial acetic acid (50 mL) in one portion. The clear yellow solution was stirred for 1 h at RT, then heated in an oil bath at 95° C. for 2 days. Water (50 mL) was added to the cooled orange solution. This solution was poured into a separatory funnel and extracted with ether (5×200 mL). The combined organic extracts were dried over anhydrous MgSO4 and concentrated to an orange oil. This oil was used without further purification.

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