Triethylsilane → [Rac]-2-methoxy-3-(4-{3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalen-1-yl)-propionic acid ethyl ester

Participants

Reaction Steps

0.228 g of the above prepared 3-hydroxy-2-methoxy-3-(4-{3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalen-1-yl)-propionic acid ethyl ester (0.44 mmol) was dissolved in 2.3 ml of trifluoroacetic acid, treated at 0° with 0.697 ml of triethylsilane (10 eq.) and then kept for 4 h at 0°. The reaction mixture was then poured onto crashed ice/AcOEt/NaHCO3, the organic layer washed twice with water, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=7/3) yielded 0.143 g of the title compound as colorless oil.

Provenance & Evidence