Water → HCID 22910718, compound

Participants

Reaction Steps

A solution of 14.4 ml of 2-(2-bromoethyl)-dioxolane and 20.6 g of (E)-2-but-1-enyl-1,3-propanediol in 200 ml of toluene was heated to slight boiling overnight with 2.7 ml of 10% aqueous sulfuric acid (v/v) and 8 ml of water. The mixture was treated with 6 ml of triethylamine and the aqueous phase was separated. The organic phase was washed with semi-conc. sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The resulting orange oil (31.3 g) was chromatographed on 400 g of silica gel with hexane/ethyl acetate 2.5% (v/v). 23.4 g of (E)-2-(2-bromoethyl)-5-but-1-enyl-1,3-dioxane (GC purity 97.5%, trans/cis ratio 73:27) were obtained as a yellowish oil.

Provenance & Evidence