1,2-Dimethoxyethane → HCID 23296058, compound

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Reaction Steps

18.2 g of methyltriphenylphosphonium bromide are suspended in 200 ml of dimethoxyethane under a nitrogen atmosphere and 1.5 g of sodium hydride (80% in paraffin) are then added in portions. The mixture is stirred at RT for 3 h and a solution of 13 g of methyl 4-methoxy-3-(4-oxotetrahydropyran-3-yloxy)benzoate are then added dropwise in the course of 30 min. The mixture is stirred overnight, then poured onto water and extracted 3 times with ethyl acetate. After drying over sodium sulfate, the organic phase is concentrated in vacuo and the residue is chromatographed on a silica gel column using ethyl acetate/petroleum ether 4:6. The chromatographically pure fractions are combined, concentrated and dried in a high vacuum. 3.6 g of the title compound are obtained as a pale yellow oil.

Provenance & Evidence