Potassium Carbonate → HCID 86704610, Verbindung

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).

1. additionThe initial cloudy mixture became clear with the addition of the base (although the base itself
2. concentrationThe solution was then concentrated in vacuo
3. customThe organic layer was separated
4. washwashed with brine (1×20 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo
7. custompurified via column chromatography on a Biotage 65i column
8. washeluting with 0% ethyl acetate in hexanes (1 CV)

ORD-Eintrag

ord-16899ceaaec443d6a7ee504c77f5ddbb

Quelldatensatz

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09221834B2