beta-Cyclocitral → Isoquinolin-7-yl(2,6,6-trimethylcyclohex-1-enyl)methanol

Participants

Reaction Conditions

Reaction Steps

A solution of 7-bromoisoquinoline (958 mg, 4.6 mmol) in tetrahydrofuran (15 mL) was added dropwise into n-butyl lithium (1.6 M in hexane, 2.87 mL, 4.6 mmol) at −78° C. and stirred at −78° C. for 30 minutes. Then 2,6,6-trimethylcyclohex-1-enecarbaldehyde (350 mg, 2.3 mmol) in tetrahydrofuran (2 mL) was added and the reaction was stirred at −78° C. for 1 hour and then allowed to warm to room temperature. The reaction was quenched with saturated aqueous ammonium chloride and the organics were extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (794 mg, Yield: 100%). Rf 0.5 (2:1 petroleum ether/ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 9.24 (s, 1H), 8.49 (d, J=5.6 Hz, 1H), 8.04 (s, 1H), 7.78 (s, 2H), 7.64 (d, J=5.6 Hz, 1H), 5.56 (s, 1H), 2.05-2.00 (m, 2H), 1.70-1.56 (m, 4H), 1.35 (s, 3H), 1.24 (s, 3H), 1.16 (s, 3H) ppm; Mass spectrum (ESI +ve) m/z 282 (M+H+).

Provenance & Evidence