Cyclooctanone → HCID 56979075, compound

Temperature

-78 °C

Cyclooctanone Compound 1a (2.5 g, 19.8 mmol) in THF (5 mL) was added dropwise to a solution of LiHMDS (23.8 mL, 23.8 mmol) in anhydrous THF (50 mL) at −78° C. under a N2 atmosphere. The mixture was stirred at −78° C. for 60 mins, then 1-bromomethyl-3-chloro-benzene Compound 3a (4.1 g, 19.9 mmol) in anhydrous THF (10 mL) was added dropwise. The mixture was stirred for 5 hrs, while warming to r.t. The reaction was quenched with water (5 mL) and the organic layer was diluted with EtOAc (100 mL), then washed with water and brine. The organic layer was separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude oil which was purified by flash chromatography using 3% EtOAc in hexane to afford 2-(3-chloro-benzyl)-cyclooctanone Compound 3b (4.12 g, 82.6%).

1. stirringThe mixture was stirred for 5 hrs
2. temperaturewhile warming to r.t
3. customThe reaction was quenched with water (5 mL)
4. additionthe organic layer was diluted with EtOAc (100 mL)
5. washwashed with water and brine
6. customThe organic layer was separated
7. dry with materialdried with anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto yield a crude oil which
11. customwas purified by flash chromatography

ORD record

ord-f4171f8c323c4111a40a8188b5d38deb

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07825151B2