Sodium hydride → HCID 66999488, compound

Participants

Reaction Steps

Sodium hydride (60% dispersion in mineral oil, 206 mg, 5.15 mmol) was added at 0° C. to a solution of (1-but-3-enylcarbamoyl-cyclopropyl)-carbamic acid tert-butyl ester (400 mg, 1.57 mmol) in tetrahydrofuran (8 ml), then after 15 min a solution of 1,2-bis(((trifluoromethyl)sulfonyl)oxy)ethane (Chem. Ber. 1981, 114, 810; 616 mg, 1.89 mmol) in tetrahydrofuran (1 ml) was added dropwise. After 1 h, another portion of sodium hydride (60% dispersion in mineral oil, 103 mg, 2.58 mmol) and after 15 min, 1,2-bis(((trifluoromethyl)sulfonyl)oxy)ethane (616 mg, 1.78 mmol) was added, and die reaction mixture was allowed to reach room temperature over 1 h, then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced the title compound (208 mg, 47%). Yellow oil, MS (ISP)=281.2 (M+H)+.

Provenance & Evidence