Indene → HCID 70015779, compound

Participants

Reaction Steps

A solution of 29.4 g of indene (0.25 mol) in 500 mL of dry hexane was reacted with 100 mL of n-butyllithium (2.5M in hexanes, 0.25 mol) at room temperature. After 2 hrs. the slurry was chilled in ice water and a solution of 24.5 g of cyclohexene oxide (0.25 mol) in 200 mL of dry hexane added during 8 hrs. After warming to room temperature the slurry was stirred overnight. The resulting mixture was treated with aqueous ammonium chloride and the resulting organic layer was separated and washed with water and then with brine. After drying over sodium sulfate, the solution was evaporated to yield 47 g of crude title compound. Purification was achieved by chromatographing in two portions using 250 g of silica gel, eluting initially with 9:1 hexane:ethyl acetate and ultimately with 2:1 hexane:ethyl acetate. The total yield of purified trans-2-(1-indenyl)-cyclohexanol was 20.0 g (0.0935 mol, 37% yield based on indene). 1H NMR (500 MHz, apparent coupling constant in Hz, CDCl3) δ7.48 (1H, m), 7.46 (1H, m), 7.29 (1H, tm, J=7.6), 7.21 (1H, td, J=7.6, 1.2), 6.34 (1H, t, 0.8), 3.84 (1H, td, J=9.89, 4.4), 3.37 (2H, m), 2.63 (1H, m), 2.14 (1H, m), 1.98 (1H, dm, J=13.4), 1.92 (1H, br s), 1.86 (1H, m), 1.76 (1H, dm, J=12.0), 1.5-1.3 (4H, m).

Provenance & Evidence