Trifluoroacetic acid → HCID 131727573, compound

Participants

Reaction Steps

To a solution of (E)-ethyl 2-(3-(benzyloxy)-3-oxoprop-1-enyl)benzoate (1.44 g, 4.64 mmol)) in 20 mL of CH2Cl2 was added N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (1.78 mL, 6.96 mmol) and trifluoroacetic acid (0.072 mL, 0.93 mmol). The solution was allowed to stir at ambient temperature for 18 h. Starting material still remained by TLC analysis and so additional N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (0.5 g, 2.1 mmol) and trifluoroacetic acid (2 drops) were added and the reaction was stirred at ambient temperature for 1 h. The reaction was evaporated and purified by ISCO (elution with 0-30% EtOAc/hexane) to afford 1.97 g (95%) of the title compound as an oil. LRMS (ES)+: 444.3 (M+H)+.

Provenance & Evidence