Nitrogen → 4-(Pyridine-3-yloxy)ethynylbenzene

Participants

Reaction Steps

4-(Pyridine-3-yloxy)benzaldehyde (0.500 g, 2.510 mmol), 4-acetamidobenzene sulfonyl azide (0.724 g, 3.01 mmol), dimethyl (2-oxopropyl) phosphonate (0.412 mL, 3.01 mmol), and potassium carbonate (1.041 g, 7.53 mmol) in MeCN (10.5 mL) and MeOH (2.1 mL) was heated to 40° C. for 16 h while under N2. The solvent was removed and residue was redissolved in EtOAc and washed with water (3×) and brine (1×). The organic phase was separated, dried with Na2SO4 and evaporated to afford an oil. This material was chromatographed on silica (0-80% EtOAc in hexanes) to yield 0.238 g as an oil.

Provenance & Evidence