first_page settings Order Article Reprints Font Type: Arial Georgia Verdana Font Size: Aa Aa Aa Line Spacing: Column Width: Background: Open AccessShort Note 5-Hydroxy-2-methyl-3-oxo-6-(2,2,3-trimethyl-cyclopent-3-enyl)-hexanoic acid ethyl ester by Mercedes Pérez-Bonilla, Juan M. Castro, Pablo J. Linares-Palomino, Sofía Salido, Joaquín Altarejos *, Manuel Nogueras and Adolfo Sánchez Departamento de Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad de Jaén, 23071 Jaén, Spain * Author to whom correspondence should be addressed. Molbank 2005, 2005(1), M396; https://doi.org/10.3390/M396 Received: 16 February 2004 / Accepted: 6 July 2004 / Published: 1 July 2005 Download Download PDF Download PDF with Cover Download XML Download Epub Download Supplementary Material Versions Notes Sodium (241 mg, 10.48 mmol) was added to absolute ethanol (40 mL) and the mixture refluxed until sodium reacted completely. Then ethyl 2-methylacetoacetate (2) (1.2 mL, 8.25 mmol) was added to the solution. The mixture was refluxed for 1 h and, then, after reaching room temperature, aldehyde 1 (1.26 g, 8.27 mmol) was added and the mixture refluxed again for 2 h. Finally, ethanol was partially evaporated under reduced pressure and the residue neutralized with aqueous 2N HCl and extracted with EtOAc (3×15 mL). The combined organic layers were washed with 2N HCl (10 mL), saturated NaHCO3 (2×15 mL) and brine (3×10 mL). The organic phase was dried over anhydrous Na2SO4 and the solvent evaporated under reduced pressure to yield a residue (1.65 g) which was purified by flash chromatography on silica gel, using a 6.5:4.5 hexane/EtOAc mixture as eluent, to give the title compound 3 (356 mg, 1.20 mmol, 15%).Melting point: 131.0–132.8 °C (white dust, from hexane/ethyl acetate).IR (neat, cm-1): 3450–2600, 1101 (OH); 3036 (C=C); 1610 (CO); 1610, 1246, 1153 (COOEt).1H NMR (300 MHz, CDCl3): δ= 0.79 (3H, s, Me-2’); 1.01 (3H, s, Me’-2’); 1.21 (3H, t, J=7.0 Hz, CH3CH2O), 1.36 (3H, d, J=6.6 Hz, Me-2); 1.62 (3H, br s, Me-3’); 1.70–2.87 (7H, m, H-4, H-6, H-1’, H-5’); 3.48 (2H, q, J=7.0 Hz, CH3CH2O); 3.61 (1H, q, J=6.6 Hz, H-2); 4.69–4.81 (1H, m, H-5); 5.24 (1H, br s, H-4’).13C NMR (75 MHz, CDCl3): δ= 169.92 (C-1); 51.68 (C-2); 201.52 (C-3); 43.98 (C-4); 73.19 (C-5); 35.25* (C-6); 7.71 (Me-2); 15.22 (CH3CH2O); 65.81 (CH3CH2O); 44.91 (C-1’); 46.79 (C-2’); 148.67 (C-3’); 121.00 (C-4’); 35.17* (C-5’); 19.73 (Me-2’); 25.46 (Me’-2’); 12.54 (Me-3’).*These signals may be interchanged.EI-MS (70 eV, m/z): 279 (M+–OH, 0.1%); 267 (M+–Et, 0.1); 251 (M+–OEt, 0.8); 235 (0.7); 217 (0.9); 205 (0.4); 193 (1); 171 (2); 161 (9); 141 (9); 133 (11); 119 (20); 108 (C8H12+, 100); 93 (29); 79 (12); 43 (34). Supplementary materialsSupplementary File 1Supplementary File 2Supplementary File 3AcknowledgementsWe wish to thank the Ministerio de Ciencia y Tecnología for financial support (R+D Project PPQ2000-1665) and the Ministerio de Educación, Cultura y Deporte for a fellowship to J. M. Castro. © 2005 MDPI. All rights reserved. Share and Cite MDPI and ACS Style Pérez-Bonilla, M.; Castro, J.M.; Linares-Palomino, P.J.; Salido, S.; Altarejos, J.; Nogueras, M.; Sánchez, A. 5-Hydroxy-2-methyl-3-oxo-6-(2,2,3-trimethyl-cyclopent-3-enyl)-hexanoic acid ethyl ester. Molbank 2005, 2005, M396. https://doi.org/10.3390/M396 AMA Style Pérez-Bonilla M, Castro JM, Linares-Palomino PJ, Salido S, Altarejos J, Nogueras M, Sánchez A. 5-Hydroxy-2-methyl-3-oxo-6-(2,2,3-trimethyl-cyclopent-3-enyl)-hexanoic acid ethyl ester. Molbank. 2005; 2005(1):M396. https://doi.org/10.3390/M396 Chicago/Turabian Style Pérez-Bonilla, Mercedes, Juan M. Castro, Pablo J. Linares-Palomino, Sofía Salido, Joaquín Altarejos, Manuel Nogueras, and Adolfo Sánchez. 2005. "5-Hydroxy-2-methyl-3-oxo-6-(2,2,3-trimethyl-cyclopent-3-enyl)-hexanoic acid ethyl ester" Molbank 2005, no. 1: M396. https://doi.org/10.3390/M396 Find Other Styles Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here. Article Metrics No No Article Access Statistics For more information on the journal statistics, click here. Multiple requests from the same IP address are counted as one view.