ethyl (E)-3-cyclopentylprop-2-enoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the method of example 54b, reaction of (E)-3-cyclopentyl-acrylic acid ethyl ester (87 g, 520 mmol) with bromine (29.3 ml, 572 mmol) and triethylamine (90 ml, 650 mmol) affords the title product as an oil (83.5 g) GC-MS (m/e): 247 (M+).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the method of example 54a, reaction of triethylphosphinoacetate (196 g, 870 mmol) with hexane-washed sodium hydride (60% in mineral oil, 35 g, 870 mmol) in THF (1200 ml) and cyclopentanecarbaldehyde (86 g, 870 mmol) in THF (300 ml) gives the title product as an oil (59.1 g). MS (m/e): 169.1 (M+H).