Boron trifluoride etherate → Spiro(4.5)decan-6-one

Participants

Reaction Steps

To a solution of bi(cyclopentane)-1,1′-diol (5.16 g, 29.4 mmol) in methylene chloride (80 mL), cooled to −20° C., was added trimethoxymethane (3.22 mL, 29.4 mmol), followed by boron trifluoride etherate (2.98 mL, 23.52 mmol). The cold bath was removed, and the reaction was stirred at ambient temperature for 2 hours. The mixture was then diluted with methylene chloride (100 mL), washed with saturated sodium bicarbonate, dried with magnesium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on silica gel (100% hexane to 15:85 ethyl acetate/hexane, eluant) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 2.40 (t, 2H), 2.00-2.11 (m, 2H), 1.78-1.87 (m, 2H), 1.71 (t, 4H), 1.59 (t, 4H), 1.39 (t, 2H); MS (DCI+) m/z 153 (M+H)+.

Provenance & Evidence