Valeryl chloride → 1-Heptyn-3-one, 1-(trimethylsilyl)-

Participants

Reaction Steps

To a stirred solution of 14.4 grams of valeryl chloride and 20.4 grams of bis-trimethylsilylacetylene in 300 ml of dry methylene chloride, cooled in an ice bath, is added powdered anhydrous aluminum chloride, portionwise, over a period of 20 minutes. The mixture is stirred for 5 minutes, then the cooling bath is removed and the mixture stirred at room temperature for 4 hours. The mixture is poured into 500 ml of ice-water. The organic layer is separated, washed with water and brine, dried over anhydrous sodium sulfate and filtered through diatomaceous earth. The mother liquor is evaporated to dryness giving a brownish residue. The residue is Kugelrohr-distilled to give 16.56 grams of colorless liquid at 45° C./0.3 mm which is essentially identical with the authentic product.

Provenance & Evidence