Diethylamine → HCID 86749181, compound

Participants

Reaction Steps

To a DMF (5 mL) solution of 1-trimethylsilyl-1,3-pentadiyne (0.4 g, 2.94 mmol) under argon was added TBAF (0.8 g, 3 mmol) and several drops of water. The dark brown solution was stirred for 2 h at room temperature, then diluted with benzene (3 mL). The benzene layer was washed with saturated brine (5×5 mL). After drying (MgSO4) and filtering, the solution was transferred to a flask containing 8 (500 mg, 0.96 mmol), (Ph3P)2PdCl2 (34 mg, 0.048 mmol), CuI (9 mg, 0.048 mmol) and Et2NH (1 mL). The mixture was stirred under argon at room temperature for 40 h, and then concentrated in vacuo. Ether (100 mL) and water (25 mL) were added, the layers were separated, the ether layer was washed with brine (3×20 mL), dried (MgSO4), concentrated in vacuo and the residue purified by flash column chromatography (1:6 CH2Cl2 :hexanes) giving 9 as a yellow oil (0.25 g, 57% yield): 1H NMR δ 7.15-7.3 (m, 10 H), 6.99 (d, J=11.7 Hz, 1 H), 6.90 (d, J=11.7 Hz, 1 H), 4.09 (s, 2 H), 4.06 (s, 2 H), 1.98 (s, 3 H), 0.20 (s, 9 H); 13C NMR δ 120-138 (several), 102.32 102.09, 84.37, 80.86, 72.45, 64.35, 37.36, 37.27, 4.82, -0.200.

Provenance & Evidence