Hydrochloric Acid → HCID 20147162, compound

Participants

Reaction Steps

To a solution of 1-octyne (5.5 g, 50 mmole) in dry THF (40 ml) at -30° C. was added n-butyl lithium in hexane (1.05 eq). After warming to 0° C. over 1 hr a solution of zinc chloride (6.95 g, 50 mmole) in THF (50 ml) was added and temperature raised to room temperature over 1/2 hr. Sequentially, solutions of 5-bromofuran-2-carboxaldehyde (8.75 g, 50 mmole) in THF (20 ml) and tetrakis triphenylphosphinepalladium (0) (5.7 g, 10%) in THF (50 ml) were added. The mixture was heated to reflux for 2 hr after which it was cooled and added to dilute hydrochloric acid (50 ml). After extracting into diethyl ether (3×100 ml), drying the ethereal solution (MgSO4) and removing the solvent under reduced pressure, the resulting oil was chromatographed on silica (DCM: Hexane 1:2) to give the title compound 6.83 g (67 %) as an oil. νmax (film) 3150, 3125, 2225, 1680, 890, 770; δ(CDCl3)0.90(3H, distorted t), 1.42(8H, complex m), 2.45(2H, t, J=6.5 Hz), 6.60(1H, d, J=3.0 Hz), 9.65(1H, s).

Provenance & Evidence