Water → HCID 178469884, compound

Participants

Reaction Conditions

Reaction Steps

Under N2, a suspension of 16 (11.5 g, 0.039 mol), NaH (60% oil dispersion, 1.64 g, 0.041 mol) and DMF (225 ml) was heated with stirring at 60° C. After 0.5 hour, a solution of ethyliodide (6.0 g, 0.039 mol) in DMF (75 ml) was added dropwise. After the addition, the reaction was allowed to stir at room temperature overnight, then poured into H2O and extracted with EtOAc (4X). The combined organic layers were backwashed with H2O, saturated Na2CO3, saturated NaCl, dried, filtered and concentrated to dryness. The residue was chromatographed on silica gel and the product eluted with 2% CH3OH-CHCl3 to yield 3.9 g (31%) of 17. An analytical sample was prepared by trituration with Et2O, mp 203°-5° C.

Provenance & Evidence