HCID 18761562, compound → HCID 18761594, compound

Participants

Reaction Steps

Employing the same general procedure as for the preparation of 2-tert-butyl-5-trimethylsilanylethynyl-1-[(4′-methyl)phenoxy]benzene (Compound U), 52 mg (0.16 mmol) 5-bromo-2-tert-butyl-1-[(4′-ethyl)phenoxy]benzene (Compound T) was converted into the title compound using mg (0.04 mmol) of bis(triphenylphosphine)palladium (II) chloride, 7 mg (0.04 mmol) of cuprous iodide, 0.2 mL (150 mg, 1.5 mmol) of trimethylsilyl acetylene and 3 mL of triethylamine. An additional 28 mg (0.04 mmol) of bis(triphenylphosphine)palladium (II) chloride, and 0.2 mL (150 mg, 1.5 mmol) of trimethylsilyl acetylene were added after 3 days of heating, and the resultant mixture was then heated at 75° C. for more days. Purification by flash chromatography (preabsorbed onto silica with 100% chloroform, eluted with 100% hexane) gave the title compound as a yellow oil. PMR (CDCl3): δ 0.19 (9 H, s), 1.25 (3 H, t, J=7.6 Hz), 1.40 (9 H, s), 2.64 (2 H, q, J=7.6 Hz), 6.86-6.92 (3 H, m), 7.12 (1 H, dd, J=1.7, 8.1 Hz), 7.17 (1 H, d, J=8.4 Hz), 7.29 (1 H, d, J=8.1 Hz).

Provenance & Evidence