Decalin → N-[1-(Benzyloxy)but-3-en-2-yl]-2,2,2-trichloroacetamide

Participants

Reaction Steps

Sodium hydride (53 mg, 2.4 mmol) was added to a solution of (2Z)-4-(benzyloxy)but-2-en-1-ol (2.0 g, 11 mmol) in THF (50 mL) at 0° C. 2,2,2-trichloroacetonitrile (1.63 g, 12 mmol) was added dropwise to the reaction mixture at 0° C. over a period of 30 minutes. The reaction mixture was stirred at room temperature for an additional 2 hours. The reaction mixture was concentrated under reduced pressure and then diluted with decahydronaphthalene (35.8 g, 259 mmol). The mixture was stirred and heated to 200° C. for 5 hours. The reaction mixture was cooled to ambient temperature, diluted with water, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to give N-[1-(benzyloxy)but-3-en-2-yl]-2,2,2-trichloroacetamide. 1H NMR (400 MHz, CDCl3) δ 7.38-7.11 (m, 6H), 5.93-5.86 (m, 1H), 5.34-5.27 (m, 2H), 4.60-4.58 (m, 3H), 3.66-3.61 (m, 2H).

Provenance & Evidence