Tetrahydrofuran → HCID 5368270, compound

Participants

Reaction Steps

Triethyl phosphonoacetate (259 mL, 1.3 mol) was added slowly drop wise to a solution of Potassium-tert-butoxide (145 g, 1.29 mol) in dry THF (2 L) at −5° C. and stirred for 30-45 mins. Then a solution of 4-(benzyloxy)benzaldehyde (Intermediate P, 230 g, 1.08 mol) in dry THF (1.5 L) was added slowly drop wise at −10° C. over a period of 15 mins and stirred for 30 mins. After completion, the reaction mixture was poured into ice water (1 L) and extracted with EtOAc (2×1.5 L). The combined organic extracts were washed with sat NaHCO3 solution (1 L), water (1 L), brine (1 L), dried over anhydrous Na2SO4, filtered and evaporated to get crude (E)-ethyl 3-(4-(benzyloxy)phenyl)acrylate (290 g, 95%). The crude was carried to next step without further purification.

Provenance & Evidence