Quinoline → HCID 69069452, compound

Participants

Reaction Steps

To a solution of 4-(5-Cyclopropyl-pent-3-ynyl)-2,2-dimethyl-[1,3]dioxolane (1.92 mmol, 0.40 g) in hexane (5 mL) was added quinoline (0.192 mmol, 24.8 mg), followed by addition of 5% Pd on BaSO4 (0.384 mmol). Stirred at room temperature under H2 atmosphere for 4 hrs. TLC showed reaction completed. Filtered through celite and concentrated. Diluted with hexane, washed with NH4Cl, brine and dried over MgSO4. Silica gel chromatography (2˜7% EtOAc/Hexane) 4-(5-Cyclopropyl-pent-3-enyl)-2,2-dimethyl-[1,3]dioxolane as clear oil 1H NMR (400 MHz, CDCl3): δ 5.52-5.45 (m, 1H), 5.40-5.34 (m,1H), 4.11-4.04 (m, 1H), 4.02 (dd, 1H, J1=8.0 Hz, J2=6.0 Hz), 3.51 (t, 1H, J=7.5 Hz), 2.17-2.04 (m, 2H), 1.97 (t, 2H, J=7.0 Hz), 1.74-1.66 (m, 1H), 1.58-1.49 (m, 1H), 1.41 (s, 3H), 1.35 (s, 3H), 0.73-0.68 (m, 1H), 0.43-0.39 (m, 2H), 0.08-0.04 (m, 2H).

Provenance & Evidence