Methyl iodide → HCID 86749276, compound

Participants

Reaction Steps

To a solution of 1M sodium bis(trimethylsilyl)amide in tetrahydrofuran (31.7 ml ) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (2.74 ml) at -78° C. was added ethyl (E) 2-{2-[2-(1,3-dihydro -4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl) ethylidene]cyclopent -1-(S)-yl}acetate (3.39 g) in tetrahydrofuran (35 ml), over a period of 30 minutes. After an additional 30 minutes methyl iodide (2.25 ml) was added. After an additional two hours saturated aqueous ammonium chloride (10 ml) and ethyl acetate were added. The organic solution was dried and evaporated and the residue chromatographed on silica gel, eluting with 4:1 hexane:ethyl acetate, to afford one diastereomer of ethyl (E) 2-{2-[2-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran -5-yl)ethylidene]cyclopent-1-(S)-yl}propionate as a low-melting solid.

Provenance & Evidence