Ammonia → ETHYL 2-(1-HYDROXYCYCLOBUTYL)ACETATE

Trimethylchlorosilane (1.14 mL, 8.92 mmol) was added by syringe to a suspension of zinc powder (7.97 g, 0.122 mol) in absolute Et2O (200 mL). The mixture was stirred for 15 minutes at room temperature, heated to reflux, the heat source was removed, and ethyl bromoacetate (10.3 mL, 92.9 mmol) was added at such a rate that the ether solution gently boiled. After being heating for one hour at reflux, the mixture was stirred for one additional hour at room temperature. A solution of cyclopentanone (6.00 g, 75.9 mmol) in ether (30 mL) was added while the temperature of the mixture was maintained at 19-20° C. by intermittent cooling. The mixture was stirred for 1 hour at room temperature and poured into iced 25% ammonia (400 mL). The aqueous phase was extracted with ether, the combined organic phases were dried over K2CO3 and the solvent was evaporated to yield the title compound as a colorless oil (6.50 g, 54%). 1H-NMR (400 MHz, CDCl3) δ 1.29 (3H, t, J=7.3 Hz), 1.47-1.64 (1H, m), 1.76-1.87 (1H, m), 1.93-2.06 (2H, m), 2.12-2.22 (2H, m), 2.67 (2H, s), 3.70 (1H, s), 4.19 (2H, q, J=7.3 Hz).

1. temperatureheated
2. temperatureto reflux
3. customthe heat source was removed
4. temperatureAfter being heating for one hour
5. temperatureat reflux
6. stirringthe mixture was stirred for one additional hour at room temperature
7. temperaturewas maintained at 19-20° C. by intermittent cooling
8. stirringThe mixture was stirred for 1 hour at room temperature
9. extractionThe aqueous phase was extracted with ether
10. dry with materialthe combined organic phases were dried over K2CO3
11. customthe solvent was evaporated

ORD-Eintrag

ord-0b636e1339084f73983e046a58beb6fc

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08901112B2