Tetrahydrofuran → HCID 21958334, compound

Participants

Reaction Conditions

Reaction Steps

An oven-dried 3-neck round bottom flask was charged with magnesium turnings (0.809 g, 0.033 mol) and 40 mL of dry THF. 5-Bromomethyl norbornene (6.001 g, 0.032 mol) was added dropwise at room temperature. The mixture was then heated to 50° C. for 18 hours. In a separate flask, 10 mL of dry THF, Li2CuCl4 (5 mL, 0.0005 mol), and 1-bromooctane (6 mL, 0.035 mol) were combined and placed in a −10° C. ice bath. The Grignard reagent, which was transferred via cannula into an addition funnel, was added dropwise to the cooled solution. After the addition was complete, the solution was warmed to room temperature and stirred for 18 hours. The solution was diluted with ether, washed with NH4Cl, brine, and dried over Na2SO4. The solvent was removed and the product was distilled at 76° C. at 0.4 mbar to yield a clear, colorless liquid (4.88 g, 69%). 1H NMR (300 MHz, CDCl3) δ6.12 (1H endo, dd, J=2.74, 5.49); 6.09–5.99 (2H exo, m); 5.93 (1H endo, dd, J=2.74, 5.49); 2.75 (1H, s); 1.98–1.78 (2H, m); 1.40–1.07 (18H, m); 0.89 (3H, t, J=6.05); 0.52–0.45 (1H, m). 13C NMR (75 MHz, CDCl3) δ137.0; 132.6; 49.7; 45.6; 42.7; 38.9; 35.0; 32.6; 32.1; 30.1; 29.9; 29.8; 29.5; 28.9; 22.9; 14.3.

Provenance & Evidence