Sodium hydride → HCID 10561223, compound

Participants

Reaction Steps

To a stirred, ice-cold solution of 559 mg (1.73 mmol) of the mesylate (18) in 10 ml of THF was added 76 mg (1.90 mmol) of a 60% dispersion of sodium hydride (NaH) in mineral oil. After 1 hour, the ice bath was removed and the reaction was stirred at room temperature. After stirring for 18 hours, another 35 mg (0.88 mmol) of a 60% dispersion of NaH was added. After 4 days of stirring, the reaction mixture was diluted with EtOAc, washed with 0.5N HCl and then with saturated NaCl, dried (MgSO4), and concentrated under reduced pressure. The resulting crude residue was flash-chromatographed on silica gel, eluting CH2Cl2. Consequently, 322 mg (82%) of the desired epoxide (19) was obtained as a colorless oil.

Provenance & Evidence