Tetrahydrofuran → HCID 12644239, compound

Participants

Reaction Conditions

Reaction Steps

A mechanically stirred suspension of copper(I) bromide-dimethylsulfide complex (20.4 g, 99.0 mmol) in 500 mL of THF was cooled to −40° C. and treated dropwise with 2.0 M solution of i-butylmagnesium chloride in THF (49.5 mL, 99.0 mmol) under an atmosphere of dry nitrogen. After stirring at −40° C. for 2 h, the reaction mixture was cooled to −78° C. and then treated dropwise with a solution of diethyl acetylenedicarboxylate (13.2 mL, 82.5 mmol) in 160 mL of THF. Upon completion of the addition, the mixture was stirred at −78° C. for 1 h, quenched with saturated NH4Cl aq., then allowed to slowly warm up to room temperature, and stirred at this temperature for additional 30 min. The organic phase was separated and the water phase was thoroughly extracted with ether. The combined organic extracts were washed with saturated NH4Cl aq., then with brine, dried over Na2SO4, and distilled in vacuum to give 14.8 g (79% yield, bp 74–75° C./1 mm Hg) of diethyl 2-1-butylmaleate as a colorless oil.

Provenance & Evidence