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 CH2Cl2 (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 CH2Cl2 (100 mL), washed with saturated NaHCO3, dried with MgSO4, and concentrated under reduced pressure. The resulting residue was chromatographed on silica gel (100% hexane to 15:85 EtOAc/hexane, eluant) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 2.40 (t, 2H), 2.00-2.11 (m, 2 H), 1.78-1.87 (m, 2 H), 1.71 (t, 4H), 1.59 (t, 4H), 1.39 (t, 2 H). MS (DCI+) m/z 153 (M+H).

Provenance & Evidence