Tetrahydrofuran → Methyl 3-(3-cyclopentoxy-4-nitrophenyl)-E-propenoate

Participants

Reaction Steps

To a stirred suspension of 0.89 g (22.3 mmol) of a 50% oil suspension of sodium hydride (previously washed with three, 10 mL portions of hexane) in 100 mL of dry tetrahydrofuran under a nitrogen atmosphere was added dropwise at room temperature 2.54 mL (15.7 mmol) of trimethylphosphonoacetate in 100 mL of dry tetrahydrofuran over a 30 minute period. The white suspension was stirred for an additional 10 minutes after which time 3.35 g (14.2 mmol) of 3-cyclopentoxy-4-nitrobenzaldehyde in 50 mL of dry tetrahydrofuran was added dropwise over a 20 minute period. The final reaction mixture was stirred for an additional hour after which time the mixture was quenched with excess saturated ammonium chloride. The mixture was extracted with three, 50 mL portions of methylene chloride and the combined organic fractions were washed with one, 50 mL portion of saturated sodium chloride, dried over magnesium sulfate and concentrated. Liquid chromatography of the crude product over 130 g of silica gel eluting with 50% ethyl acetate in hexane provided the desired, analytically pure solid.

Provenance & Evidence