Dimethyl Sulfoxide → SB-200473

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To a suspension of sodium chloride (315 g, 5.39 mol) and deionized water (315 mL) was added the dimethyl sulfoxide (4.2 L) solution of 2-carbomethoxy-4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-1-one (323 g, 0.87 mol) and the resulting suspension was heated to 155° C. for 1.75 h. The reaction was cooled to 40° C., was quenched into 8 L of iced water (2° C.) and was extracted with ethyl acetate (3.5 L). The aqueous layer was isolated and re-extracted with 2.5 L of ethyl acetate. The combined organic extract (6 L) was washed two times with deionized water (2×1 L) and once with brine (1 L). The organic layer was isolated and concentrated in vacuo to afford a residue. This residue was dissolved in refluxing isopropanol (500 mL), was cooled to 0° C. and held at this temperature for 1 hour. The crystals were isolated by filtration, were washed with 250 mL of isopropanol (0° C.), and were dried in a vacuum oven (45° C. at 20 inches) to produce 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one. m.p. 111-112° C.; Anal. (C19H23NO3) calcd: C 72.82, H 7.40, N 4.47; found: C 72.72, H 7.39, N 4.48.

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