Tetrahydrofuran → HCID 11334330, compound

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.

1. stirringstirred for 30 min
2. extractionextracted with EtOAc (2×300 mL)
3. washThe combined organic extracts were washed with saturated NaHCO3 solution (250 mL), water (250 mL) and brine (250 mL)
4. dry with materialdried over anhydrous Na2SO4
5. filtrationfiltered
6. customevaporated

ORD record

ord-2c7667f586c34f57b8efdc34f70dab85

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006449B2