Diethylamine → HCID 15199168, compound

Participants

Reaction Steps

A mixture of CuI (4.7 mg. 0.02 mmol), bis(triphenylphosphine) palladium (II) chloride (7.7 mg, 0.01 mmol), Et2NH (2 mL), trimethylsilylethyne (80 mL, 0.546 mmol), 6 (100 mg, 0.182 mmol), and dry benzene (1.5 mL) was stirred for 48 h at room temperature under argon in a flask wrapped with aluminum foil. Analysis by TLC (1:4 CH2Cl2 :hexanes) indicated the disappearance of starting compound. The solution was concentrated in vacuo, and water (10 mL) and ether (25 mL) were added to the residue. The layers were separated, the aqueous layer was extracted with ether (2×10 mL), the combined ether layers were washed with water (2×10 mL), dried (MgSO4), and concentrated in vacuo. Flash column chromatography of the residue (2.5:97.5 ethyl acetate: hexanes) afforded 12 as a pale yellow solid (63.3 mg, yield 71%): 1H NMR δ 7.2-7.5 (m, 12 H), 6.97 (s, 2 H), 4.15 (s, 4 H), 0.25 (s, 18 H); 13C NMR δ 137.76, 131.83, 128.92, 128.58, 128.27, 121.15, 102.43, 101.78, 37.37, -0.09; Anal. Calcd for C28H34S2Si2, C, 68.51; H, 6.98. Found, C, 68.57; H, 7.02.

Provenance & Evidence