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Synthesis of a 2,3-dihydrobenzofuran analoguea
aReagents and conditions: (a) n-BuLi, THF, −78 °C, 3 h; (b) 5-bromo-2-methoxybenzaldehyde, THF, RT, overnight; (c) SOCl2, CH2Cl2, reflux, 3 h; (d) AgCN, CH3CN, reflux, 5 h; (e) 3-chloro-N,N-dimethylpropan-1-amine, LDA, THF, reflux 1.5 h; (f) HBr/H2O, reflux, overnight; (g) LiAlH4, ether, 0 °C to RT, 2.5 h; (h) MsCl, NEt3, 0 °C, 3 h.
