Cyclopentene → 3,3'-Dicyclopentyl-5,5',6,6',7,7',8,8'-octahydro-2,2'-binapthol

Beteiligte Stoffe

Reaktionsschritte

A mixture of 5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binapthol (48 g), phosphotungstic acid (2.4 g) and cyclopentene (58 g) was charged into a Hastelloy reactor. The reactor was heated to 180 C for 40 hours. The mixture was purified by column chromatography (silica gel, eluting with 2% ethyl acetate/hexane) to yield 29.5 g (42%) of 3,3′-dicyclopentyl-5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binapthol, mp 143–152° C. 13C NMR (CDCl3): 22.96, 25.31, 26.68, 29.19, 32.72, 32.75, 39.20, 118.58, 128.14, 129.20, 129.74, 133.91, 149.14 ppm. 1H NMR (CDCl3): 1.60 (m, 10H), 2.0 (d, 4H), 2.65 (t, J=4 Hz, 2H), 3.27 (quintet, J=7 Hz, 1H), 4.55 (s, 1H), 6.92 (s, 1H) ppm.

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