Distannoxane, 1,1,3,3-tetrabutyl-1,3-dichloro- → 3-chloro-6-cyclopentyl-6-[2-(3-fluoro-4-isopropoxyphenyl)ethyl]-4-hydroxy-5,6-dihydro-2H-pyran-2-one

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Reaction Steps

A solution of methyl 2-chloro-5-cyclopentyl-7-(3-fluoro-4-isopropoxyphenyl)-5-hydroxy-3-oxoheptanoate (1.74 g, 4.1 mmol), and bis(dibutylchlorotin)oxide (1.38 g, 2.5 mmol), dissolved in toluene (20 mL) were heated at reflux for 30 mins. The resulting mixture was concentrated and purified by silica gel chromatography to give the title compound (0.80 g, 50% yield, two Steps). 1H NMR (300 MHz, CDCl3): δ 1.33 (d, J=6.03 Hz, 6H), 1.45-1.80 (m, 10H), 1.99-2.05 (m, 2H), 2.34-2.44 (m, 1H), 2.59-2.66 (m, 2H), 4.44-4.52 (m, 1H), 6.78-6.91 (m, 3H).

Provenance & Evidence