Chloromethyl Methyl Ether → HCID 68649319, compound

Participants

Reaction Steps

A solution of annonacinone (595 mg, 1.0 mmol) in diisopropylethylamine (7 mL) is stirred at room temperature while chloromethyl methyl ether (360 mg, 4.5 mmol) is added. The mixture is stirred at room temperature for eight hours, concentrated in vacuo, and the residue is partitioned between water (50 mL) and ethyl acetate (50 mL). The aqueous phase is separated and extracted with ethyl acetate (2×50 mL) and the combined organic fractions are washed (1× water), dried (saturated aqueous NaCl, sodium sulfate), filtered, and concentrated. Chromatography (hexane-2:1 hexane:ethyl acetate gradient over silica gel 230-400 mesh) affords 3-{2,13-bis(methoxymethyloxy)-13-[tetrahydro-5-(1-methoxymethyloxytridecyl) furan-2-yl]tridecan-8-on-1-yl}-5-methyl-2-(5H)-furanone.

Provenance & Evidence