Tetrahydrofuran → 2-methyl-4-[(2-methyl-1-oxo-2,3-dihydro-1H-inden-4-yl)sulfanyl]-1-indanone

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Reaction Steps

Under an argon atmosphere, following the procedure described for bis(2-methyl-1H-inden-7-yl)sulfide, 22.9 g (85.2 mmol) of the above-described dioxalane-protected 4-bromo-2-methylindanone in 150 ml of THF, 34.1 ml of 2.5 M (85.3 mmol) nBuLi in hexanes, and 4.39 g (42.6 mmol) of SCl2 in 35 ml of hexanes gave crude dioxalane-protected 2-methyl-4-[(2-methyl-1-oxo-2,3-dihydro-1H-inden-4-yl)sulfanyl]-1-indanone, which was deprotected in a mixture of 150 ml of 16 M HCl and 150 ml of methanol for 7 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 35 mm, l 400 mm, eluant: CH2Cl2) and then recrystallized from hexanes. Yield, 3.53 g (26%) of a white solid.

Provenance & Evidence