Tetrahydrofuran → HCID 22728827, compound

Temperature

17.5 °C

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).

1. customwere placed into a 250 ml 4-neck round bottom flask
2. customequipped with a mechanical stirrer and a reflux condenser
3. additionwere added dropwise to the stirred solution at a rate which
4. temperaturemaintained the pot temperature between 15-25° C
5. customquenched at 5° C. with the addition of 60 ml of water and neutralized at pH 7
6. customThe organic layer was separated
7. distillationThe resulting crude product was fractionally distilled with a bulb-to-bulb distillation (0.5 mbar, 120° C.)

ORD record

ord-7b76e21beeb24466abd120ef7741c357

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06720295B2