Pentane → HCID 22037817, compound

Temperature

-60 °C

A mixture of 2-cyclopentylacetonitrile (0.50 g, 4.59 mmol) in tetrahydrofuran (10 mL) was cooled to −60° C. then treated with 1.7 M tert-buytllithium in pentane (3.25 mL, 5.50 mmol) while maintaining the reaction temperature at less than −55° C. The solution was stirred for 10 minutes then ethyl formate (0.41 g, 5.50 mmol) was added dropwise. The mixture was warmed to ambient temperature and stirred an additional 16 hours. The mixture was concentrated under reduced pressure and the resulting residue applied to a silica gel column and eluted with dichloromethane/ethyl acetate (95:5). The fractions containing material with an Rf of 0.1–0.3 [TLC, dichloromethane/ethyl acetate (95:5), potassium permanganate stain) were combined and concentrated to give an oil which was used without further purification: 1H NMR (Chloroform-d, 400 MHz) δ 9.57 (s, 1H), 3.54 (d, 1H), 2.45 (m, 1H), 1.4–1.9 (m, 8H).

1. temperaturewhile maintaining the reaction temperature at less than −55° C
2. temperatureThe mixture was warmed to ambient temperature
3. stirringstirred an additional 16 hours
4. concentrationThe mixture was concentrated under reduced pressure
5. washeluted with dichloromethane/ethyl acetate (95:5)
6. additionThe fractions containing material with an Rf of 0.1–0.3 [TLC, dichloromethane/ethyl acetate (95:5), potassium permanganate stain)
7. concentrationconcentrated
8. customto give an oil which
9. customwas used without further purification

ORD record

ord-a7df8718c86049db81c9d8953d000404

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07071199B1