3-Acetylpyridine → HCID 86751250, compound

Participants

Reaction Conditions

Reaction Steps

To a separate flask was added 3-acetylpyridine (0.27 g, 0.0021 mol) in THF (10 ml) and the solution cooled under N2 to -78° C. To this solution was added dropwise via syringe at -78° C. lithium diisopropylamide (1.1 ml of a 2M solution in heptane-THF-ethylbenzene, 0.0022 mol). After aging for 5 min., the imidazolide solution was added dropwise at -78° C. The resulting thick suspension was then allowed to stir to room temperature. After 2 h, the clear yellow solution was poured into saturated NaHCO3 solution and the aqueous layer was extracted with EtOAc (3×). The organic extracts were dried, filtered and concentrated to dryness. The crude residue was chromatographed on a Still column (40 mm) and the product eluted with 10% IPA/CHCl3 saturated with NH3 to yield 1-(tetralin-2-yl)-4-(1-(3-hydroxy-1-oxo-3-(3-pyridinyl)-2-propenyl)piperdine.

Provenance & Evidence