By R. J. Adams
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Substituted Amides. Lukes87 has obtained ethyl l-methyl-2-pyrrolone-5-acetate in about 20% yield by treating N-methyl succinimide with ethyl bromoacetate and zinc. CH=C—CH2CO2C2H5 N CH 3 \ BrCH 2 CO 2 C 2 H 6 Zn N—CH 3 CH 2 —CO VARIATIONS OF THE REFORMATSKY REACTION Use of Halogen Compounds Other Than a-Haloesters. Aromatic aldehydes react with /S- and 7-bromo- and iodo-esters in the presence of zinc, but the yields are very low (1 to 3%). 101 Certain reactive halogen compounds, other than a-haloesters, have been found to condense with aromatic aldehydes in the presence of zinc.
18 CH2COC1 CH2CO—CHN* CH2CH2CO2CHS CH2CH2CO2H CH2CH2CO2C2H6 CH2CH2CO2C2Hii CH2CH2CO2C2H6 CH2CH2CO2H The A r n d t - E i s t e r t reaction is ideal for use on complex molecules. T h e reaction is carried o u t a t moderately low temperatures so t h a t t h e chances of decomposing t h e molecule are n o t as great as in some of t h e other syntheses. A n interesting example in t h e synthesis of t h e sex hormone equilenin is t h e conversion of one of t h e intermediates t o its next higher homolog in good yield (80-84%).
To this is added, with continuous cooling and efficient stirring or swirling, 15 g. of finely powdered JV-nitrosomethylurea in small portions as rapidly as the crystals dissolve (a few minutes). The deep yellow ethereal solution of diazomethane can be separated from the aqueous layer by decantation or by means of a separatory funnel. 2 g. of diazomethane, is dried for several hours over pellets of pure potassium hydroxide or over soda-lime. A solution of diazomethane in benzene may be prepared in the same way.