Diethyl Ether → 3-Benzyl-3-trichloroacetamidocyclopentene

A solution of compound 3-benzyl-2-cyclopentenol (3.0 g, 17.2 mmol) in ether (50 mL) was added to a suspension of hexane washed 60% NaH (468 mg, 11.7 mmol) in ether (50 mL) at 0° C. under N2 and stirred for 1 h. Trichloroacetonitrile (3.0 g, 20.8 mmol) was slowly added and the resulting mixture was allowed to warm to ambient temperature and stirred overnight. The solvent was removed in vacuo, hexane (25 mL) was added and the mixture was cooled to 0° C. Methanol (1 mL) was added and the resulting solid was filtered through Celite. The organic solvent was removed in vacuo to give a crude intermediate (3.2 g). This intermediate was dissolved in xylene (0.1 L) and heated to reflux for 3 h under N2. The solvent was removed in vacuo, and the residue was purified by column on silica gel (100 g, EtOAc/hexane (1:9), to give the title compound (1.8 g, 33%) as a white crystal: mp 127-128° C.;

1. stirringstirred overnight
2. customThe solvent was removed in vacuo, hexane (25 mL)
3. additionwas added
4. temperaturethe mixture was cooled to 0° C
5. additionMethanol (1 mL) was added
6. filtrationthe resulting solid was filtered through Celite
7. customThe organic solvent was removed in vacuo
8. customto give a crude intermediate (3.2 g)
9. temperatureheated
10. temperatureto reflux for 3 h under N2
11. customThe solvent was removed in vacuo
12. customthe residue was purified by column on silica gel (100 g, EtOAc/hexane (1:9)

ORDレコード

ord-6b22be5fa43843fa98856b06a68ece86

出典データセット

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06667309B2