Acetone → HCID 86677538, compound

Participants

Reaction Steps

To a solution of the above compound (4.10 g, 16.9 mmol) in a 200 mL of a 2:1:1 mixture of THF:acetone:water was added sodium periodate (10.9 g, 50.8 mmol) and osmium tetroxide (4% aqueous solution, 6.65 mL, 0.847 mmol) dropwise. After 2 hours, the reaction was diluted with ethyl acetate, washed with water, aqueous sodium thiosulfate, and brine. The organic solution was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-20% ethyl acetate in hexanes to provide methyl 4-formyl-1-methoxy-2-naphthoate that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 245.2 for [M+H]+.

Provenance & Evidence