2,2'-Bipyridine → HCID 20427189, compound

Participants

Reaction Steps

To THF (250 ml) under N2 with stirring is added cyclopentane-1,3-dione (0.10 mol) and 2,2'-bipyridyl (~3-5 mg) as an indicator. After cooling to -70°, n-butyllithium in hexane is added slowly while the temperature is allowed to rise to -5° near the end of the addition (~130 ml of 1.6 M solution, 0.20 mol). After the pink indicator persists at -5°, the mixture is recooled to -65° and 4-(4-trifluoromethylphenoxy)phenoxyacetyl chloride is added dropwise over 5 min. After 1 hour, the reaction mixture is diluted with water and ether is added. The organic layer is washed with water, dried over sodium sulfate and concentrated in vacuo to give 2-[4-(4-trifluoromethylphenoxy)phenoxyacetyl]cyclopentane-1,3-dione (V; Y is H, Z is CF3, R1 is H and n is one).

Provenance & Evidence