Tetrahydrofuran → tert-Butyl cyclopentylacetate

Participants

Reaction Steps

136 ml of a 1 M solution of potassium tert-butoxide in THF (136 mmol) were cooled to 0° C., and 21.0 g (143.2 mmol) of cyclopentylacetic chloride were added dropwise. After the addition had ended, the suspension was warmed to RT and stirred overnight and then added to saturated aqueous ammonium chloride solution. The mixture was extracted three times with diethyl ether. The combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. The desired product was isolated from the residue by kugelrohr distillation (1.6 mbar/160-180° C.). This gave 17.58 g of the target compound (66.6% of theory).

Provenance & Evidence