Methyl Acrylate → HCID 14773942, compound

Participants

Reaction Steps

1-Methyl-1H-indole-3 carboxamide oxime (C. J. Swain et al, J Med Chem, 1991, 34, 147) (0.500 g, 2.64 mmol) was dissolved in dry THF (20 ml) with stirring, and treated with ground 4A molecular sieves (1.5 g) under nitrogen. After 30 minutes sodium hydride (80% dispersion in mineral oil) (0.087 g, 2.91 mmol) was added. The mixture was then heated to reflux. After 30 minutes the mixture was allowed to cool momentarily and a methyl acrylate (0.475 ml, 5.28 mmol) was added. The mixture was then heated to reflux for a further 3 hours. The reaction mixture was then allowed to cool and was filtered. The filter pad was then washed with THF (2×). The filtrate was then evaporated under reduced pressure. The residue was purified by silica-gel chromatography eluting with pentane EtOAc 3:1 to afford the title compound (D2) as a colourless oil that crystallised on standing rapt 53°-55° C.

Provenance & Evidence