P,P-Diphenylphosphinic azide → 3-(1-Azidotridecyl)-2-triethylsilylfuran

Participants

Reaction Steps

Reacting 3-(1-hydroxytridecyl)-2-triethylsilylfuran (Compound 20) with diphenylphosphoryl azide and diethyl azidocarboxylate gives 3-(1-azidotridecyl)-2-triethylsilylfuran (Compound 24). Reducing this intermediate with lithium aluminum hydride, followed by acetylation with acetic anhydide gives 3-(1-acetamido tridecyl)-2-triethylsilylfuran (Compound 25). Singlet oxygen oxidation of this amide, under conditions as in Example 1, followed by reduction with sodium borohydride gives 3-(1-acetamidotridecyl)-2(5H)-furanone (Compound 10).

Provenance & Evidence