2-(Dimethylamino)ethanol → 6-(2-Dimethylaminoethoxy)-1-tetralone

Participants

Reaction Steps

To a mixture of 6-hydroxy-1-tetralone (Aldrich, 1.0 g, 6.17 mmol, 1.0 eq), N,N-dimethylethanolamine (Aldrich, 0.93 mL, 9.26 mmol, 1.5 eq), and triphenylphosphine (Aldrich, 2.43 g, 9.26 mmol, 1.5 eq) in THF (10 mL) was added diethyl azodicarboxylate (Aldrich, 1.94 mL, 12.34 mmol, 2.0 eq) at 0° C. The reaction mixture was gradually warmed to RT and continued to stir overnight. The solvent was evaporated in vacuo. The residue was purified by silica gel chromatography (3%-5% MeOH—CH2Cl2) to provide the product as orange oil. MS (ESI): 234 (M+H)+.

Provenance & Evidence