2-(Dimethylamino)ethanol → (2-[4-(Tert-butyl)-2-nitrophenoxy]-ethyl)dimethylamine

Participants

Reaction Steps

DEAD (2.6 mL) was added to a mixture of 2-nitro-4-tert-butylphenol (2 g) and N,N-dimethylethanolamine (1.3 g) and Ph3P (4 g) in THF (50 mL). The reaction was stirred at RT for 1 h, diluted with EtOAc (50 mL) and washed with 1 N HCl twice. The aqueous layer was basified with NaHCO3, extracted with EtOAc twice and washed with H2O and brine. The organic layer was dried over Na2SO4 and evaporated to give (2-[4-(tert-butyl)-2-nitrophenoxy]ethyl)-dimethylamine. It was hydrogenated under H2 atmosphere to give {2-[4-(tert-butyl)-2-aminophenoxy]ethyl}-dimethylamine.

Provenance & Evidence