3-hydroxy-2-iodo-4-methoxybenzaldehyde

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-hydroxy-2-iodo-4-methoxybenzaldehyde (2.5 g, 8.99 mmol) in methanol (30 ml) was added potassium carbonate (3.11 g, 22.48 mmol) and methyl diethylphosphonoacetate (1.980 ml, 10.79 mmol). The initial cloudy mixture became clear with the addition of the base (although the base itself was mostly insoluble) The mixture was stirred overnight at 55° C. and became yellow and cloudy again. The solution was then concentrated in vacuo and the residue was taken up in ethyl acetate (20 mL) and 1M HCl (aq) (20 mL). The organic layer was separated and washed with brine (1×20 mL), dried over sodium sulfate, concentrated in vacuo, and purified via column chromatography on a Biotage 65i column eluting with 0% ethyl acetate in hexanes (1 CV) followed by a gradient to 50% ethyl acetate in hexanes (over 7 CV) to furnish the desired product as the E olefin. 1H NMR (CDCl3, 500 MHz) $ 7.95 (d, J=15.9 Hz, 1H), 7.14 (d, J=8.4 Hz, 1H), 6.74 (d, J=8.6 Hz, 1H), 6.27 (d, J=15.8 Hz, 1H), 3.91 (s, 3H), 3.80 (s, 3H), 2.34 (s, 3H). The initial cloudy mixture became clear with the addition of the base (although the base itself The solution was then concentrated in vacuo The organic layer was separated washed with brine (1×20 mL) dried over sodium sulfate concentrated in vacuo purified via column chromatography on a Biotage 65i column eluting with 0% ethyl acetate in hexanes (1 CV)