Diisopropylamine → 289652-61-5

Participants

Reaction Steps

To a solution of 1.2 g of 2-bromothiophene and 0.9 g of butynol in 15 ml of degassed dioxane were added 100 mg of PdCl2(PheCN)2, 50 mg of CuI, 1 ml of diisopropyl amine, 750 μl of a 1M solution of tri-tert-butyl phosphine in toluene. The mixture was stirred under N2 atmosphere for 16 hr and then diluted with 50 ml of water and extracted with ethyl acetate. The organic layers were combined and washed with water, dried and concentrated. The residue was chromatographed using a gradient of heptane/ethyl acetate as eluent, to provide 850 mg of 1a; Rf (heptane/ethyl acetate 1/1) 0.50. NMR (CDCl3) δ 1.83 (t, 1, OH), 2.72 (t, 2, CH2), 3.83 (q, 2, CH2), 6.95, 7.16, 7.20 (3×m, 3, thiophene-H).

Provenance & Evidence