Beta-Nitrostyrene → HCID 86605367, compound

Participants

Reaction Steps

To a solution of nitrostyrene 23 (14.9 g, 0.1 mol) in tetrahydrofuran (100 mL) was added solid O-methylhydroxylamine hydrochloride (9.2 g, 0.11 mol) and sodium hydrogen carbonate (9.24 g, 0.11 mol). The reaction mixture was diluted with water (25 mL) and stirred at room temperature overnight under argon. The reaction mixture was mixed with ethyl acetate (150 mL) and washed with water (1×50 mL). The aqueous layer was back washed with ethyl acetate (1×50 mL). The combined organic layers were washed with brine (1×75 mL), filtered through 1PS filter paper and stripped to give 18.6 g (95% yield) of 34I as brown oil. Hplc analysis showed a purity of 98%. NMR (CDCl3) δ 7.5(S, 5H), 6.1(S br, 1H), 4.5–5.1(m, 3H), 3.5(S, 3H).

Provenance & Evidence