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. The mixture was then 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. The mixture was refluxed one hour then stirred for an 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. After being one hour of stirring at room temperature, the mixture was poured into iced 25% ammonia (400 mL). The aqueous phase was extracted with ether and the combined phases were dried over K2CO3. Filtration and evaporation of the solvent yielded 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. temperatureThe mixture was then heated
2. temperatureto reflux
3. customthe heat source was removed
4. temperatureThe mixture was refluxed one hour
5. stirringthen stirred for an additional hour at room temperature
6. temperaturewas maintained at 19-20° C. by intermittent cooling
7. waitAfter being one hour
8. stirringof stirring at room temperature
9. extractionThe aqueous phase was extracted with ether
10. dry with materialthe combined phases were dried over K2CO3
11. filtrationFiltration and evaporation of the solvent

ORD record

ord-3faaa0c991184448aed2a118baf15158

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901112B2