Triethylamine → 2,3-Di(2-methanesulfonyloxyethyl)furan

Participants

Reaction Steps

A solution of the product from step d.) (3.58 g, 22.9 mmol) in CH2Cl2 (114 ml), was cooled to 0° C., and treated with triethylamine (9.56 ml, 68.7 mmol) followed by dropwise addition of methanesulfonyl chloride (3.88 ml, 50.4 mmol) over 10 minutes. After 1 hour, the reaction mixture was transferred to a separatory funnel and extracted with ice water (1×50 ml), 10% citric acid (2×50 ml), sat. NaHCO3 (2×50 ml) and brine (1×50 ml). The organic layer was dried (MgSO4), concentrated to 20 ml, diluted with dry dioxane (42 ml) and further concentrated to remove remaining CH2Cl2. The resulting dioxane solution of the bismesylate was immediately carried into step f)

Provenance & Evidence