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they melted at 227°and agreed in all other characteristics with the alkaloid obtained from the valves.This procedure was much more satisfactory than the immiscible-solvent method used in isolating the alkaloid from the valves. It was carried out more quickly, was less wasteful, and yielded a crude alkaloid that was more easily purified. It should be especially useful in the isolation of alkaloids that are quite soluble in water and that are not reduced by hydrogen sulfide. SummaryA new alkaloid has been isolated from Lupinus spathulatus, a plant that occurs in Utah and Colorado. The new base has been named spathulatine and has been assigned the formula C33H64O5N4. The properties of the free alkaloid and the preparation of its mercuric iodide compound which may serve as a microchemical test are described.

In a previous paper2 it was shown that when 2-butanone reacts with n-butyraldehyde the condensation takes place through the methylene group of the ketone. This is also the case in its reaction with formaldehyde3 and a~etaldehyde.~ On the other hand Thoms and Kahre6 have shown that the reaction between 2-butanone and isobutyraldehyde yields 2methyl-3-heptene-5-one1 (CH&CHCH=CHCOCzH6. In view of this difference in behavior it seemed desirable to investigate the reaction between 2-butanone and other aldehydes.It was found that the condensation of 2-butanone with propionaldehyde, n-valeraldehyde and n-heptaldehyde takes place through the methylene group of the ketone. From these results and those previously obtained in the cases of formaldehyde, acetaldehyde and n-butyraldehyde, it appears that the normal aliphatic aldehydes in general react in this manner with 2-butanone. As Thoms and K a h e have shown that the branched-chain isobutyraldehyde brings about a different reaction, an investigation of the reaction between 2-butanone and other branched-chain aldehydes is now under way.The constitution of the condensation product was determined in each case by dehydration of the aldol to the unsaturated ketone and reduction of this to the corresponding saturated alcohol. In the case of propionaldehyde this saturated alcohol was iound to be identical with the 3-methyl-2hexanol described by Bjelouss6 and on oxidation yielded a ketone identical with the 3-methyl-2-hexabone obtained by the hydrolysis of ethyl methyln-propyl-acetoacetate. The striictures of the alcohols obtained from nvaleraldehyde and n-heptaldehyde were determined by oxidation and identification of the resulting acids as n-valeric and enanthic acids, respectively. The condensation, dehydration, reduction to the saturated alcohol, and oxidation of this to the saturated ketone were carried out as described in the previous paper.2In Table I are listed the new compounds prepared. Identification of the Acids Obtained by Oxidizing 3-Methyl-2-octanol and 3-Methyl-2-decanol.-The alcohols were oxidized by boiling with a (1) This paper is based in part upon lheses presented by Hazel C. Murray and Maynard M.Baldwin in partial fulfilment of the requirements for the Master's degree.