Triethylamine → 1-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-phenyl-acetic acid methyl ester

Participants

Reaction Steps

To a white suspension of 1-(4,5-dimethoxybenzyl)6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-hydrochloride (5 g, 0.013 mol) in dry toluene (50 ml), were added triethylamine (5.5 ml, 0.039 mol) and bromo-phenyl-acetic acid methyl ester (2.07 ml, 0.013 mol). The reaction mixture was stirred at reflux under argon for 20 h. After cooling, the mixture was diluted in CH2Cl2 and washed with water. The aqueous phase was extracted twice with CH2Cl2, the combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give a crude brown-orange oil. Flash chromatography (AcOEt/hexane 1/1) gave 5.85 g (90%) of the title product as a brown-orange oil.

Provenance & Evidence