Triethylamine → 5-Isocyano-2,3-dihydroinden-1-one

Participants

Reaction Steps

A mixture of 5-amino-2,3-dihydroinden-1-one (5) and butyl formate (5 eq.) was allowed to reflux overnight. The reaction mixture was then concentrated to an oil which solidified upon standing. The crude material [N-(1-oxo-2,3-dihydro-1H-inden-5-yl)formamide (15.00 g, 73 mmol)] was suspended in cold (0° C.) THF (300 mL) and triethylamine (81 mL, 582 mmol). To this was slowly added 6.6 mL (1 eq.) of POCl3. HPLC after 2 hours showed almost complete conversion. The crude reaction mixture was added to silica gel and concentrated (the bath temp was kept at about 25° C.), and the concentrated mixture was loaded onto a silica column. The product was eluted with DCM (100%) to give 5-isocyano-2,3-dihydroinden-1-one (6).

Provenance & Evidence