Water → HCID 68847579, compound

Participants

Reaction Steps

2-(3,5-Dichlorophenoxy)-N-(1-hydroxymethyl-4-methylpent-2-yn-4-yl)butyramide (prepared as described in Example 2; 1.54 g) in dry N,N-dimethylformamide (20 ml) was added dropwise over 5 minutes to a suspension of sodium hydride (0.28 g, 80% dispersion in mineral oil) in dry N,N-dimethylformamide (2 ml) under an atmosphere of nitrogen at ambient temperature. The mixture was stirred for 2 hours and methyl iodide (0.71 g) in dry N,N-dimethylformamide (5 ml) was added over 1 minute at ambient temperature. The mixture was stirred for 2 hours and stored at ambient temperature for 18 hours. Water was added and the mixture extracted with ethyl acetate (three times). The extracts were combined, washed with water (twice), dried over magnesium sulphate and evaporated under reduced pressure to give a gum that was fractionated by chromatography (silica; hexane/ethyl acetate, 4:1 by volume) to give the required product (0.44 g) as a colourless solid, mp 103-104° C.

Provenance & Evidence