Trimethylsilylacetylene → HCID 12079586, compound

Participants

Reaction Conditions

Reaction Steps

4-Iodo-N,N-dihexylaniline (3.150 g, 8.13×10−3 mol), Pd(PPh3)2Cl2 (0.332 g, 4.73×10−4 mol), CuI (0.130 g, 6.83×10−4 mol) and Et3N (20 ml) were added to a 100-ml round-bottom flask. Ar was bubbled into the reaction mixture for 5 min before (trimethylsilyl)acetylene (2.40 ml, 1.70×10−2 mol) was added. The reaction mixture was stirred at 45° C. for 18 h under Ar. After the solvent was removed in vacuo, the residue was chromatographed on silica gel 4:1 hexane:CHCl3 as the eluent. Yield=2.861 g (98% based on 3.150 g of 4-iodo-N,N-dihexylaniline). 1H NMR (250 MHz, CDCl3): δ 7.29 (d, 2H, J=9.0 Hz, Ph), 6.50 (d, 2H, J=9.0 Hz, Ph), 3.24 (t, 4H, J=7.7 Hz, —NCH2—), 1.43-1.65 (m, 4H, —NCH2CH2—), 1.19-1.41 (m, 12H, —CH3—), 0.89 (t, 6H, J=6.5 Hz, —CH3), 0.22 (s, 9H, Si—CH3). CI MS m/z: 358.292 ((M+H)+) (calcd 358.293).

Provenance & Evidence