Ethylene Oxide → HCID 10512306, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 ml flask were placed 11-2 (0.500 g, 3.16 mmol), and anhydrous THF (6 mL). The reaction was flushed with N2 gas and cooled to −78° C. Ethylene oxide (27.3 g, 31 mL, 31.6 mmol) was added dropwise via syringe. Upon completion of addition, the reaction mixture was warmed to room temperature and stirred for 18 hours. The reaction mixture was then quenched with sat. aq. NH4Cl (100 mL) and extracted with EtOAc (2×150 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel flash column chromatography (24 g cartridge), eluting with 0-100% EtOAc/hexanes to give 200 mg (31%) of 11-3. LC/MS: m/z (M+H)=203.2.

Provenance & Evidence