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0 °C

To a stirred solution of N-methoxy-N-methyl-3-(3-cyclopentyloxy-4-methoxyphenyl)prop-2-enamide (1.986 g, 6.50 mmol) in dry tetrahydrofuran (15 ml) at -78° C. was added methyl lithium (1.4M solution in hexanes, 10.20 ml, 14.3 mmol) dropwise over 3 minutes. The resulting solution was stirred for 1 hour at 0° C., after which time the reaction mixture was diluted with 5% HCl in methanol (20 ml) at 0° C., and partitioned between brine (35 ml) and an equal volume of methylene chloride and diethyl ether (100 ml). The organics were dried (Na2SO4) and concentrated in vacuo to give a light yellow oil. The oil was purified by flash chromatography (SiO2 ; ethyl acetate/hexane (35:65)) to afford the title compound as a colorless oil (1.642 g).

1. custompartitioned between brine (35 ml)
2. dry with materialThe organics were dried (Na2SO4)
3. concentrationconcentrated in vacuo
4. customto give a light yellow oil
5. customThe oil was purified by flash chromatography (SiO2 ; ethyl acetate/hexane (35:65))