Sodium hydride → HCID 15351906, compound

Participants

Reaction Steps

NaH (0.72 g, 30 mmol) is stirred with absolute DMF (12 ml) at RT and then 4,5α-epoxy-3-methoxymethoxy-17-methyl-morphinan-7-en-6α-ol (1.9764 g, 6 mmol) in DMF (12 ml) is added. After the development of gas has ceased, a solution of ethyl 2-chloro-nicotinate (5.568 g, 30 mmol) in absolute DMF (8 ml) is added at RT. After 1 hour at RT this reaction mixture is poured onto H2O (100 ml) and extracted 3 times with CH2Cl2 (60 ml). The combined organic phases are dried with Na2SO4, concentrated by rotary evaporation and the residue is purified by flash chromatography (90 g silica gel, CH2Cl2MeOH=9/1). Yield: 2.53 g (5.29 mmol, 88%)

Provenance & Evidence