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. 2017 Jan;21(3):218–235. doi: 10.2174/1385272820666160928120822

Scheme 5.

Scheme 5

Synthesis of formononetin with applications of olefin metathesis. Reagents and conditions: a) POCl3, DMF, MeCN,0-50o C, then H2O, 50o C; b) BnCl, KI, NaHCO3, MeCN, reflux; c) Wittig reaction: methyltriphenylphosphine bromide (MTPPB), t- BuOK, 0oC, 2h; THF, 1 h; 2-bromo-4'-methoxyacetophenone, reflux,1h; d) MTPPB, t- BuOK, 0oC, 2h; e) Grubbs 2nd, CH2Cl2, 40oC, 8 h; f) BH3–SMe2, THF, 0oC, 4 h, then H2O, 10% NaOH, 37% H2O2, 30 min; g) DDQ, 1,4-dioxane, reflux, 8 h; h) Pd(OH)2, EtOH, cyclohexene, reflux, 1 h.