Water → Ethyl cyclopentylideneacetate

Participants

Reaction Steps

To a flame-dried 500-mL round-bottomed flask containing NaH (5.10 g of a 60% dispersion in mineral oil, 128 mmol, 1.10 equiv) in 120 mL anhydrous THF at 0° C. under argon was added triethylphosphonoacetate (25.6 mL, 128 mmol, 1.10 equiv) dropwise through an addition funnel. The mixture was allowed to warm to rt, stirring for an additional 1 h. A solution of cyclopentanone (10.3 mL, 116 mmol) in 10 mL anhydrous THF was added dropwise over 20 min through an addition funnel, and the mixture was allowed to stir at rt for 2.5 h. Ether (200 mL) and water (100 mL) were then added, and the layers were separated. The organic phase was washed successively with water (100 mL) and brine (100 mL), dried (Na2SO4), and concentrated under reduced pressure, giving 17.5 g (98%) of the desired ester as a colorless oil.

Provenance & Evidence