Triphenylphosphine → 3-(Trimethylsilyl)ethynylbenzaldehyde

Participants

Reaction Steps

3-Bromobenzaldehyde (30 g, 162 mmol), ethynyl-trimethylsilane (30 mL, 211 mmol), triphenylphosphine (2.13 g, 8 mmol), palladium (II) acetate (0.91 g, 4 mmol) and triethylamine (540 mL, 0.3 M) were heated at 90° C. for 5 hours, after cooling to ambient temperature, the mixture was filtered. The filtrate was evaporated, and the residue was subjected to silica gel chromatography (hexane to 4:96 diethyl ether/hexane) to afford 3-trimethylsilanylethynyl-benzaldehyde 73(a1).

Provenance & Evidence