Tetrahydrofuran → HCID 86660539, compound

Participants

Reaction Steps

A solution of triethylamine (2.5 mL), THF (20 mL) and 2-mercaptopyridine (0.77 g, 6.95 mmol) was stirred for 15 minutes at 0° C. A solution of undec-10-enoyl chloride (X) (1.17 g, 5.79 mmol) in THF (20 mL) was added all at once. Immediately the reaction was then quenched by adding an aqueous HCl-solution (2.0 M, 50 mL) at 0° C. and subsequently extracted with diethyl ether. The organic phase was separated and the aqueous phase was extracted with diethylether. The combined organic phases were washed with a saturated bicarbonate solution and brine, dried over MgSO4 and evaporated under reduced pressure to give a yellow oil. The crude green oil was purified by column chromatography using silica gel (eluent CH2Cl2). The compound (XI) was obtained as a lightly yellow oil. (0.64 g, 40%). 1H-NMR (CDCl3): δ=8.60-8.55 (m, 1H), 7.73-7.65 (m, 1H), 7.60-7.54 (m, 1H), 7.27-7.20 (m, 1H), 5.84-5.68 (m, 1H), 5.01-4.84 (m, 2H), 2.65 (t, J=7.5 Hz, 2H), 1.99 (q, J=13.7 Hz, J=6.7 Hz, 2H), 1.73-1.61 (m, 2H), 1.40-1.17 (m; 10H).

Provenance & Evidence