Cycloheptanone → HCID 58882506, compound

Temperature

-78 °C

Cycloheptanone Compound 1a (3.0 g, 26.8 mmol) in THF (5 mL) was added dropwise to a solution of LDA (17.6 mL, 31.7 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-fluoro-benzene Compound 1b (5.0 g, 26.5 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-fluoro-benzyl)-cycloheptanone Compound 1c (4.72 g, 80%).

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-b952e644d31543de9c3d0ee1211a5584

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08378117B2