Styrene Oxide → 2-allylamino-1-phenyl-ethanol

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Reaction Steps

A mixture of styrene oxide (24 mL, 0.2 moles) and allylamine (60.8 mL, 0.8 moles) was heated to reflux under nitrogen atmosphere, for 24 hours. Upon cooling, product crystallized and was triturated with hexane. Recrystallization from hexane afforded the title compound essentially uncontaminated by the other possible regioisomer. Ms m+/z=177; H1NMR (CDCl3): δ 7.3 (br.s, 5H), 5.6-6.1 (m, 1H), 4.9-5.4 (m, 2H), 4.75 (m, 1H), 3.2 (br.d, 2H), 2.9 (br.s, 2H), 2.7 (m, 2H).

Provenance & Evidence