Triphenylphosphine → HCID 20157919, compound

Participants

Reaction Steps

Palladium acetate (60 mg) was added to a deaerated solution of methyl 3-(2-bromophenyl)propanoate (11.10 g, 25 mmole), 1-tridecyne (6.75 g) and triphenylphosphine (200 mg) in anhydrous triethylamine (100 ml) and the mixture was stirred at reflux under nitrogen for 24 hrs. After cooling, the precipitated triethylamine hydrobromide was filtered off and the filtrate was evaporated to a red oil. Chromatography on silica eluting with 1:1 dichloromethane-petrol (bp 60°-80° C.) gave the title product, 1.91 g (22%) as an oil, νmax (film) 2920, 2850, 1745 cm-1, δ(CDCl3) 0.84 (3H, distorted t, terminal CH3), 1.28 (18H, m, alkylene chain), 2.39 (2H, t, J 7 Hz; C=C--CH2), 2.62 (2H, m, ArCH2), 3.04 (2H, m, CH2CO2), 3.62 (3H, s, ester CH3), 7.12 (3H, m, arom), 7.31 (1H, m, arom).

Provenance & Evidence