Nitrogen → HCID 66846604, compound

Participants

Reaction Steps

To the ethyl propynoate (Aldrich, 3.96 g, 40 mmol) in THF (200 mL) in a 3-neck, 3-L round bottom flask equipped with an addition funnel, internal thermometer, and N2 inlet at 0° C. was added trifluoroacetic acid (TFA) (Aldrich, 0.3 mL, 4 mmol). Benzyl(methoxymethyl)trimethylsilylmethylamine (Aldrich, 23.7 g, 100 mmol) in 50 mL THF was added dropwise via addition funnel over 30 minutes with the reaction temperature being maintained below 5° C. After the addition was complete, the mixture was allowed to warm slowly to ambient temperature and then was stirred for 10 h. The mixture was concentrated and the residue was dissolved in 500 mL EtOAc. It was washed with 2×50 mL saturated NaHCO3 and 25 mL brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, 50% hexanes-EtOAc) to give 14.5 g of the title compound (36.6 mmol, 91% yield). MS (DCl/NH3) m/z 365 (M+H)+.

Provenance & Evidence