Hydrochloric Acid → HCID 69593807, compound

Participants

Reaction Steps

1,4-Dioxane (40 mL), tri-t-butylphosphine (0.182 g, 0.9 mmol), and methyldicyclohexylamine (19.5 g, 100 mmol) were placed into a Schlenk flask and transferred by syringe to a PPI LC series 300 mL reactor containing dipalladium tris(dibenzylidenelacetone) (0.420 g, 0.45 mmol) and 4-bromonapthoyltrifluoroacetone (10.4 g, 30 mmol) under an argon atmosphere. The reactor was charged to 300 psi with ethylene and the reaction was allowed to stir for 48 hours at room temperature. Upon completion of the reaction the contents taken up in water (50 mL) and ether (50 mL), the aqueous phase acidified by addition of concentrated hydrochloric acid, and extracted with ether (2×50 mL). The combined organic phase was rinsed with saturated sodium chloride solution, and the organic phase was dried over magnesium sulfate overnight. The solution was filtered, the solvent was removed by vacuum, and the residue dissolved in chloroform (3 mL). The product was isolated by column chromatography from silica gel (Selecto, mesh size 63-200) with 10% ether in chloroform as eluent. The solvent was removed to give a light brown oil (9.08 g, 99% yield). 1H-NMR (90 MHz, 25° C., CDCl3): δ 14.49 (s, 1H), 8.48 (m, 1H), 8.06 (m, 1H), 7.58 (m, 4H), 7.45 (dd, 1H), 6.45 (s, 1H), 5.91 (dd, 1H), 5.62 (dd, 1H). Anal.: (found/calc for C17H14O2) 65.75 (81.58), H 3.79 (5.59).

Provenance & Evidence