反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: A 50 mL round-bottom flask was charged with catechol (499 mg, 4.53 mmol), CH3CN (4.5 mL), and Cs2CO3 (1.50 g, 4.60 mmol) and purged with nitrogen. This white suspension was allowed to stir for 10 minutes prior to the addition of 1-iodo-2-methylpropane (1.67 g, 9.06 mmol). The reaction was brought to reflux and allowed to stir for 18 h. After cooling to room temperature the solvent was concentrated in vacuo, and the residue partitioned between ethyl acetate (50 mL) and 1 N HCl (50 mL). The organic layer was separated, dried, filtered, and concentrated in vacuo. Flash chromatography (3:1 hexane:ethyl acetate) afforded a yellow oil weighing 316 mg (30% yield). 1H NMR (CDCl3): δ 1.05 (dd, J=1.95 Hz, J=6.85 Hz, 6H), 2.13 (s-7, J=6.60 Hz), 3.81 (d, J=6.60 Hz), 6.81-6.88 (m, 3H), 6.93-6.95 (m, 1H); 13C NMR (CDCl3): δ 19.39, 28.38, 75.31, 111.77, 114.57, 120.22, 121.12, 121.44, 146.16.
purged with nitrogen
to reflux
to stir for 18 h
was concentrated in vacuo
the residue partitioned between ethyl acetate (50 mL) and 1 N HCl (50 mL)
The organic layer was separated
dried
filtered
concentrated in vacuo
Flash chromatography (3:1 hexane:ethyl acetate) afforded a yellow oil
来源 ID: ord-d970d7715482482a942eedeb6ad3bd36