Tetrahydrofuran → HCID 22728827, compound

Participants

Reaction Conditions

Reaction Steps

31.3 ml of a 2.8 M solution of EtMgCl in THF (87.7 mmol), diluted with 50 ml of anhydrous ether were placed into a 250 ml 4-neck round bottom flask, equipped with a mechanical stirrer and a reflux condenser. Upon cooling to 15-20° C., 6 g (35.16 mmol) of 3-cyclopentylpropionic acid ethyl ester (obtained according to Barret et al., J. Chem. Soc.; 1935, 1065) dissolved into 50 ml of anhydrous ether were added dropwise to the stirred solution at a rate which maintained the pot temperature between 15-25° C. The reaction mixture was then stirred at room temperature overnight and then quenched at 5° C. with the addition of 60 ml of water and neutralized at pH 7. The organic layer was separated and the ether and THF were stripped at reduced pressure. The resulting crude product was fractionally distilled with a bulb-to-bulb distillation (0.5 mbar, 120° C.) to give 4.5 g of pure 5-cyclopentyl-3-ethyl-3-pentanol (66% yield).

Provenance & Evidence