Water → HCID 69292771, compound

Temperature

-70 °C

A solution of cycloheptylcarboxaldehyde (1.89 g, 15 mmol) in dry THF (10 mL) was added dropwise at −70° C. to a solution of 2-fluoro-3-lithiopyridine (prepared from 2-fluoropyridine (1.3 ml, 15 mmol) and LDA (16.5 mmol); Guengoer T., Marsais F., Queguiner G., J. Organomet. Chem. (1981), 215 (2), 139-150) in THF (30 ml). After 2 h30 at −70° C., the reaction was stirred at room temperature during 16 hours. Hydrolysis was performed by addition of water, the mixture was then diluted with ether. After separation of the two layers, the ether solution was washed with brine, dried over Na2SO4 and evaporated in vacuum to yield a viscous oil. The alcohol was dissolved in CH2Cl2 (50 ml) at room temperature and PCC (6.46 g, 30 mmol) was added. After 16 hours, the mixture was filtered on a pad of Celite and concentrated. The residual oil was chromatographied on silica gel (CH2Cl2/hexane 75/25) and the cycloheptyl(2-fluoro-3-pyridinyl)methanone 40 was isolated as a colorless oil (780 mg, 24%).

1. customHydrolysis
2. customAfter separation of the two layers
3. washthe ether solution was washed with brine
4. dry with materialdried over Na2SO4
5. customevaporated in vacuum
6. customto yield a viscous oil
7. waitAfter 16 hours
8. filtrationthe mixture was filtered on a pad of Celite
9. concentrationconcentrated

ORD record

ord-39901709bf1e44b98f24b7b56b1eb3be

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361668B2