Ammonium Chloride → HCID 86759699, compound

Participants

Reaction Steps

3-Bromofuran (5.88 g, 40 mmol) was dissolved in anhydrous tetrahydrofuran (60 ml) and the solution cooled to −78° C. n-Butyllithium (2.29M, 17.5 ml, 40 mmol) was added dropwise and the solution stirred for 1 h at −78° C. [3-(Methoxymethylamino)-3-oxopropyl]carbamic acid, 1,1-dimethylethyl ester as a solution in tetrahydrofuran (40 ml) was added dropwise over 1 h. The solution was stirred overnight whilst allowing to warm to room temperature. Aqueous saturated ammonium chloride solution (30 ml) was added and the mixture extracted with ethyl acetate (3×70 ml). The combined organic extracts were washed with water (3×30 ml), dried (sodium sulphate) and evaporated in vacuo. The residue was chromatographed on flash silica, eluting with hexane:ethyl acetate (7:3), to afford the title compound as a pale yellow solid (3.03 g, 63%).

Provenance & Evidence