HCID 86689406, compound → HCID 68028053, compound

Participants

Reaction Conditions

Reaction Steps

1,4-Bis-(3-hexyl-undec-1-ynyl)-2,5-dimethoxy-benzene (4.3) (7.70 g, 12.1 mmol) is dissolved in tetrahydrofuran (200 cm3) under an atmosphere of Argon. 10% Pd/C (1.25 g) is added, the mixture warmed to 30° C. (oil bath temperature) and stirred under an atmosphere of hydrogen for 2.5 hours. The reaction mixture is filtered through a plug of celite and the plug washed through with ethyl acetate (2×50 cm3), and the filtrate is concentrated in vacuo. The crude oil is purified by column chromatography eluting with 2 to 5% ethyl acetate in petroleum ether (40-60° C.). A second purification by column chromatography is carried out, eluting with 3% ethyl acetate in petroleum ether (40-60° C.) to give the title product as a colourless oil (7.00 g, 90%). NMR (1H, 400 MHz, CDCl3): δ 6.65 (s, 2H); 3.78 (s, 6H); 2.53 (m, 4H); 1.51 (m, 4H); 1.28 (m, 50H); 0.89 (m, 12H)

Provenance & Evidence