Cyclopentanone → HCID 13593934, compound

Temperature

-60 °C

To a solution of tert-butyl acetate (5.0 g, 42.8 mmol,) in THF (20 mL) was added lithium diisopropylamide (21.4 mL, 42.8 mmol) at −60° C. After stirred at −60° C. for 30 min, cyclopentanone (3.0 g, 35.7 mmol) was added at −60° C. The reaction was stirred 1 h; then it was quenched with aqueous ammonium chloride (5 mL) at −60° C. and the mixture was warmed to room temperature. The reaction was partitioned between ethyl acetate and water. The combined organic layer was dried over sodium sulfate, filtered and concentrated to give a crude product which was purified by column chromatography eluting with petroleum ether/ethyl acetate (3:1) to give tert-butyl 2-(1-hydroxycyclopentyl)acetate (5.0 g, 70.1% yield) as a yellow oil.

1. stirringThe reaction was stirred 1 h
2. customthen it was quenched with aqueous ammonium chloride (5 mL) at −60° C.
3. temperaturethe mixture was warmed to room temperature
4. customThe reaction was partitioned between ethyl acetate and water
5. dry with materialThe combined organic layer was dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customto give a crude product which
9. customwas purified by column chromatography
10. washeluting with petroleum ether/ethyl acetate (3:1)

ORD record

ord-e2dc53858a314331aef1449ba85d1dd8

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359359B2