Tetrahydrofuran → methyl 3-(3-cyclopentoxy-4-methoxyphenyl)-E-propenoate

Participants

Reaction Steps

To a stirred suspension of 7.5 g (0.16 mol) of a 50% oil suspension of sodium hydride (previously washed with three, 10 mL portions of hexane) in 600 mL of dry tetrahydrofuran under a nitrogen atmosphere was added dropwise at room temperature 16.5 mL (0.10 mol) of trimethylphosphonoacetate in 100 mL of dry tetrahydrofuran over a 20 minute period. The white suspension was stirred for an additional 2 hours after which time 20.4 g (0.09 mol) of 3-cyclopentoxy-4-methoxybenzaldehyde in 150 mL of dry tetrahydrofuran was added dropwise over a 10 minute period. The final reaction mixture was stirred for an additional hour after which time the mixture was quenched with 75 mL of saturated sodium chloride. After separation of the solvent layers, the organic fraction was dried over sodium sulfate and concentrated. Liquid chromatography of the crude product over 250 g of silica gel with 20% ethyl acetate in hexane provided the desired, analytically pure product upon crystallization from hexane.

Provenance & Evidence