Ethyl bromoacetate → HCID 19736718, compound

Participants

Reaction Steps

A mixture of 5,7-dihydroxy-spiro [2H-1-benzothiine-2,1'-cyclohexan]-4(3H)-one (prepared in Preparation 79) (0.47 g, 1.78 mmol ), ethyl bromoacetate (0.297 g, 1.78 mmol), anhydrous potassium carbonate (0.368 g, 2.67 mmol), and dry acetonitrile (5 ml) is stirred overnight at room temperature. The mixture is stirred at 35° C. for additional 5 hours. The reaction mixture is filtered to remove inorganic materials. The solvent is removed by distillation from the filtrate. The residue is placed on a silica gel column and eluted with a mixture of dichloromethane and ethyl acetate (9:1) to obtain ethyl 2-{(5-hydroxy-3,4-dihydro-4-oxospiro[2H-1-benzothiine-2,1'-cyclohexan]-7-yl)oxy}acetate as a crystalline solid (0.57 g, 91.5%). Recrystallization from diethyl ether gives a product having a melting point of 87°-88° C.

Provenance & Evidence