Dimethylformamide → N,N-Dimethyl-2-[2-(2-naphthyl)ethenyloxy]ethanamine

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Reaction Steps

Table 1, Entry 7. In the reaction tube were mixed 2-naphthyl triflate (0.276 g, 1.0 mmol), [2-(dimethylamino)ethoxy]ethene (0.23 g, 2.0 mmol), palladium acetate (0.00673 g, 0.030 mmol), triphenylphosphine (0.0173 g, 0.066 mmol) triethylamine (0.202 g, 2.0 mmol) and 0.75 ml DMF.under nitrogen. The contents of the flask were irradiated for 7.00 min with an effect of 35 W. After cooling, the product mixture was diluted with 50 ml pentane, transferred to a separatory funnel and washed with 2×25 ml water. Additional extraction of the aqueous phases was performed with 25 ml pentane. The combined organic portions were then treated 5 times with 20 ml of 0.1 M HCl. The aqueous extracts were combined, poured into a flask containing excess NaOH (1.0 M) and was extracted with 2×50 ml pentane. The combined organic phases were dried (K2CO3) and concentrated by evaporation. The yield was 87% (yellow oil, trans/cis 1/1).

Provenance & Evidence