Diethyl Ether → (1-Formylcyclopropyl)carbamic acid tert-butyl ester

Participants

Reaction Steps

To a 0.05 M solution of [1-(methoxy-methyl-carbamoyl)cyclopropyl]carbamic acid tert-butyl ester in Et2O (80 mL, 4.0 mmol) at room temperature was added dropwise lithium aluminum hydride (1.0 M in Et2O, 5 mL, 5.0 mmol). The reaction mixture was stirred for another 20 min and then quenched with 6 mL of a solution of KHSO4 in water. The layers were separated and the aqueous layer was extracted with Et2O. The combined organic layers were washed with 1 N HCl, saturated NaHCO3, and brine, dried (Na2SO4), and concentrated to yield (1-formylcyclopropyl)carbamic acid tert-butyl ester as a colorless oil (393 mg) which was used immediately in the next step without further purification.

Provenance & Evidence