Water → 5-Cyclopenten-1-ylpyridine-3-carboxaldehyde

Temperature

-60 °C

A solution of 3-bromo-5-cyclopenten-1-ylpyridine (9) (1 g, 4.5 mmol) in 25 ml of ether is added to a solution of n-butyllithium (1.6M in hexane, 4.2 ml, 6.7 mmol) in 25 ml of ether kept at −60° C. The reaction mixture is stirred for 2 h 30 min at −60° C. and then 1.4 ml of 4-morpholinecarboxaldehyde (13.4 mmol) are added. The reaction is stirred for 1 hour at −60° C. and then poured into water, the organic phase is washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 80/20). The title product is obtained in the form of a beige solid (0.38 g).

1. customkept at −60° C
2. stirringThe reaction is stirred for 1 hour at −60° C.
3. washthe organic phase is washed with a saturated aqueous sodium chloride solution
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue is purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 80/20)

ORD record

ord-b5437d123c6a4b43afb5d421c0b06394

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07235568B2