Name: Diethyl cyclobutane-1,1-dicarboxylate《Preparation of hydantoins containing a cycloalkyl substituent》 was published in 1952. The authors were Henze, Henry R.;Gayler, Cecil Winston, and the article was included in《Journal of the American Chemical Society》. The author mentioned the following in the article:
(BrCH2)2CH2 was converted in 56% yield to Br(CH2)3CN, b5 75°, b754 208°, nD25 1.4752, d425 1.4810, and this further in 77% yield to CH2.CH2.CHCN (I), b20 35-9°, b755 133-5°, nD25 1.4208, d425 0.9131. PhMgBr (from 32 g. PhBr) in Et2O and 11 g. I yielded 15.7 g. (78.5%) CH2.CH2.CHCOPh (II), b20 125°, nD20 1.5525, d425 1.1456. Similarly was prepared CH2.CH2.CHCO(CH2)2CHMe2 (III), 68%, b4 69-70°, nD20 1.4395, d420 0.8790; 2,4-dinitrophenylhydrazone, m. 95°. CH2.(CH2)2.C(CO2Et)2, b10 106-7°, nD20 1.4335, d420 1.0350, was prepared in 44% yield from (BrCH2)2CH2, CH2(CO2Et)2, and NaOEt, hydrolyzed with alc. KOH, and the dicarboxylic acid decarboxylated at 210° to give 68% CH2.(CH2)2.CHCO2H (IV), b8 88-90° b754 190°, nD20 1.4400, d420 1.0470. IV treated with SOCl2 yielded 85% CH2.(CH2)2. CHCOCl (V), b750 137°. V gave with C6H6 and AlCl3 35-55% CH2.(CH2)2.CHBz, (VI), b8 122-5°, b750 260-2°, nD20 1.5415, d420 1.0467. AcNH2 (100 g.), 0.14-0.3 mol. KCN in its own weight of H2O, 0.1-0.2 mol. II, III, or VI, and 0.3-0.6 mol. (NH4)2CO.3 heated 20 hrs. in a glass-lined steel bomb at 110-25° and the mixture cooled, diluted with 100-200 cc. H2O, and acidified yielded the following 5,5-disubstituted hydantoins (substituents given): 56% CH2.CH2.CH, Ph, m. 211.5° (corrected); 15% CH2.CH2.CH, iso-Am, m. 176-7° (corrected); and 85% CH2.(CH2)2.CH, Ph (VII), m. 234.5-5° (corrected), resp. Catalytic hydrogenation of VII with PtO in EtOH yielded 70% 5-cyclobutyl-5-cyclohexylhydantoin, m. 254-5° (corrected). AcNH2 (175 g.), 27 g. 2-methylcyclopentyl Me ketone, 19.5 g. KCN, and 62 g. (NH4)2CO3 heated 10 hrs. in a closed container at 110° and the product fractionally crystallized from Me2CO yielded 9 g. (17%) trans-5-(2-methylcyclopentyl)-5-methylhydantoin (VIII), white plates, m. 228-30° (corrected), and 34% cis-isomer (IX) of VIII, white needles, m. 176-7° (corrected). In a similar run carried out in 50% EtOH at 65°, the yields of VIII and IX were 41% each. 2,3-dimethylcyclopentyl Me ketone was converted similarly in 50% EtOH medium to 62% 5-(2,3-dimethylcyclopentyl)-5-methylhydantoin, which was separated by fractionated crystallization into 2 isomers, m. 145-50° and 220-5°. And Diethyl cyclobutane-1,1-dicarboxylate (cas: 3779-29-1) was used in the research process.
Diethyl cyclobutane-1,1-dicarboxylate (cas:3779-29-1
) is a solid catalyst that can be used in the synthesis of alkylating agents. It is used in the manufacture of cyclopropyl ketones and has been shown to exhibit anticancer properties.
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