Aluminum(III) Chloride → HCID 66927220, compound

Participants

Reaction Steps

To a slurry of LiAlH4 (419 mg, 11.03 mmol) in anhydrous THF at 0° C. under a nitrogen atmosphere was added AlCl3 (488 mg, 3.67 mmol) and the reaction mixture was stirred for 10 min. To this slurry was then added compound 6-3 (500 mg, 1.47 mmol) and stirring continued for 30 min by which time MS showed no starting material. The reaction was quenched by adding water, extracted by ether, dried, and concentrated. The crude material was purified by column chromatography to give compound 6-4 (480 mg, 90%) as a white solid. 1H NMR (CDCl3, 300 MHz) δ (ppm) 2.42 (s, 6H), 2.58 (dd, 1H, J=12.4, 9.6), 2.71 (dd, 1H, J=12.4, 3.3), 3.89 (s, 3H), 4.08 (s, 3H), 5.28 (dd, 1H, J=9.2, 3.0), 6.33 (d, 1H, J=8.5), 6.97 (s, 1H), 7.20 (d, 1H, J=8.3). APCI [M+1]: 309, 311, 327, 329.

Provenance & Evidence