Water → 5-Acetylthiomethyl-5-ethyl-2,2-dimethyl-1,3-dioxane

Participants

Reaction Steps

Sodium hydride (340 mg., 50% dispersion in paraffin oil) was added carefully to a stirred solution of thiolacetic acid (500 mg.) in dry dimethylformamide (100 ml.) at 20°. After 30 minutes 2,2-dimethyl-5-ethyl-5-iodomethyl-1,3-dioxane (2.0 g.) was added. The mixture was refluxed with stirring for 2 hours. The mixture was cooled and poured into water. The aqueous mixture was extracted with ether. The ethereal extracts were washed with water and dried over anhydrous magnesium sulphate. The solution was evaporated in vacuo. The residue was purified by column chromatography on silica, eluting with 1:4 ether:hexane. 5-Acetylthiomethyl-5-ethyl-2,2-dimethyl-1,3-dioxane was obtained as a pale yellow oil (1.5 g.)

Provenance & Evidence