Methyl vinyl ketone → 5-Amino-2-butyl-6-fluoro-2-(3-oxobutyl)-1-indanone

Participants

Reaction Steps

A solution of 5-amino-2-butyl-6-fluoro-1-indanone (0.98 g, 4.64 mmol) in ethanol (17 mL) was treated with sodium methoxide (0.5M solution in MeOH, 1.86 mL, 0.928 mmol) and methyl vinyl ketone (0.579 mL, 6.97 mmol). The resulting solution was stirred at room temperature and under a nitrogen atmosphere for 2 days. The mixture was diluted with CH2Cl2 and filtered through a pad of silica gel. The product washed off with EtOAc and the filtrate was evaporated under vacuum. The residue was purified by flash chromatography on a Biotage 40M KP-Sil column, eluting with 3:1 to 2.5:1 hexanes-EtOAc. The product containing fractions were evaporated under vacuum to provide to afford 5-amino-2-butyl-6-fluoro-2-(3-oxobutyl)-1-indanone(0.6 g, 46%) as a yellow foam.

Provenance & Evidence