5-Indanecarboxaldehyde → 2,3-Dihydro-5-(2-methyl-1-propen-1-yl)-1H-indene

Participants

Reaction Conditions

Reaction Steps

In a flamed dried flask under argon isopropyltriphenylphosphonium iodide (6.48 g, 15 mmol) in 30 mL of dry THF was cooled to 0° C. Then n-BuLi (2.5 M) in hexanes (6.0 mL) was added via syringe. The reaction mixture was stirred 0° C. for 45 min. Then a solution of the 2,3-dihydro-1H-indene-5-carboxaldehyde (J. Med. Chem. 1993, 36, 3700–3706) was added (1.7, 12.0 mmol) in THF (20 mL) was added drop-wise and the reaction was stirred under Argon at RT overnight. The reaction was filtered, the filtrate was concentrated in vacuo and the residue purified by flash colum chromatography (ethyl acetate/hexane, 1:99) to yield the above titled compound as a pale yellow oil (1.7 g, 67%).

Provenance & Evidence