Tetrahydrofuran → HCID 11334330, compound

Participants

Reaction Steps

Triethyl phosphonoacetate (26.6 g, 118.8 mmol) was added slowly dropwise to a mixture of Potassium-tert-butoxide (14.5 g, 129.6 mmol) in dry THF (200 mL) at −5° C., stirred for 20 min and then a solution of 6-bromopyridine-3-carboxaldehyde (20 g, 108 mmol) in dry THF (100 mL) was added slowly dropwise at −5° C. and stirred for 30 min. After completion, the reaction mixture was poured into ice water (350 mL) and extracted with EtOAc (2×300 mL). The combined organic extracts were washed with saturated NaHCO3 solution (250 mL), water (250 mL) and brine (250 mL) and dried over anhydrous Na2SO4, filtered and evaporated to get (E)-ethyl 3-(6-bromopyridin-3-yl)acrylate (20 g, 72.9%) as brown color liquid. This is carried to next step without further purification.

Provenance & Evidence