Tetrahydrofuran → HCID 59457447, compound

Temperature

-78 °C

Compound 1b (7.0 g) was added to a solution of LHMDS (1M, 50 mL) in THF (50 mL) at −78° C. The mixture was stirred for 30 mins at −78° C. and then 1-bromomethyl-3-fluoro-benzene Compound 1c (8.80 g, 46.55 mmol) in THF (10 mL) was added dropwise. The mixture was stirred for 24 hrs while warming to room temperature. The reaction mixture was quenched with 1N HCl (5 mL), diluted with H2O (100 mL) and EtOAc (500 mL) and the organic layer was washed with brine, separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude oil. Purification by flash chromatography (10% EtOAc in Hexane) to provide 2-(3-fluoro-benzyl)-cyclopentanone Compound 1d (5.20 g, 27.05 mmol, 58% yield) as a yellow oil.

1. stirringThe mixture was stirred for 24 hrs
2. temperaturewhile warming to room temperature
3. customThe reaction mixture was quenched with 1N HCl (5 mL)
4. additiondiluted with H2O (100 mL) and EtOAc (500 mL)
5. washthe organic layer was washed with brine
6. customseparated
7. dry with materialdried with anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto yield a crude oil
11. customPurification by flash chromatography (10% EtOAc in Hexane)

ORD record

ord-44d471cddcad427ca88676644675b9f5

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119621B2