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3-Methyl-3-(6,6,6a-trimethyl-hexahydro-cyclopenta[b]furan-2-yl)-butan-2-one

Departamento de Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad de Jaén, 23071 Jaén, Spain
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Author to whom correspondence should be addressed.
Molbank 2005, 2005(1), M393; https://doi.org/10.3390/M393
Submission received: 16 February 2004 / Accepted: 30 March 2004 / Published: 1 July 2005
Molbank 2005 m393 i001
A 40% aqueous solution of sulfuric acid (0.5 mL) was added to a stirred solution of 3,3-dimethyl-4-hydroxy-5-(2,2,3-trimethyl-3-cyclopentenyl)-pentan-2-one (1) (630 mg, 2.65 mmol) in methanol (5 mL) and the mixture refluxed for 1.5 h. The resulting solution was partially evaporated under reduced pressure, resolved in Et2O and washed with saturated Na2CO3 (3×25 mL) and brine (3×25 mL). The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to give a crude, which was filtered through a silica gel pad to yield the cyclized and rearranged title compound 2 (504 mg, 2.11 mmol, 80%) as a yellow liquid.
IR (neat, cm-1): 1705 (CO), 1077, 906 (C-O-C).
1H NMR (300 MHz, CDCl3): δ= 0.82 (3H, s, Me-6’); 0.96 (3H, s, Me’-6’); 1.03 (3H, s, Me-6a’); 1.05 (3H, s, Me-3); 1.09 (3H, s, H-4); 1.16-1.28 (1H, m, H-4’); 1.35 (1H, dd, J=12.2 Hz, 8.1 Hz, H-5’); 1.50-1.63 (2H, m, H-3’, H’-5’); 1.78-1.88 (1H, m, H’-3’); 1.90-2.06 (1H, m, H’-4’); 2.20 (3H, s, H-1); 2.31-2.42 (1H, m, H-3a’); 3.97 (1H, dd, J=11.5 Hz, 4.7 Hz, H-2’).
Some signals were assigned by means of 2D NMR experiments.
13C NMR (75 MHz, CDCl3): δ= 26.87 (C-1); 213.73 (C-2); 50.09 (C-3); 18.53 (C-4); 21.82 (Me-3); 84.68 (C-2’); 34.81 (C-3’); 46.84 (C-3a’); 29.33 (C-4’); 40.54 (C-5’); 46.43 (C-6’); 94.96 (C-6a’); 22.08 (Me-6’); 25.23 (Me’-6’); 19.60 (Me-6a’).
Some signals were assigned by means of 2D NMR experiments.
EI-MS (70 eV, m/z): 238 (M+, 0.2%); 223 (M+–Me, 0.4); 195 (M+–COMe, 0.1); 153 (M+–C5H9O, 15); 109 (10); 96 (22); 86 (47); 71 (13); 55 (13); 43 (CH3CO+, 100).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

We 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.

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MDPI and ACS Style

Castro, J.M.; Porras, R.; Linares-Palomino, P.J.; Salido, S.; Altarejos, J.; Nogueras, M.; Sánchez, A. 3-Methyl-3-(6,6,6a-trimethyl-hexahydro-cyclopenta[b]furan-2-yl)-butan-2-one. Molbank 2005, 2005, M393. https://doi.org/10.3390/M393

AMA Style

Castro JM, Porras R, Linares-Palomino PJ, Salido S, Altarejos J, Nogueras M, Sánchez A. 3-Methyl-3-(6,6,6a-trimethyl-hexahydro-cyclopenta[b]furan-2-yl)-butan-2-one. Molbank. 2005; 2005(1):M393. https://doi.org/10.3390/M393

Chicago/Turabian Style

Castro, Juan M., Ramón Porras, Pablo J. Linares-Palomino, Sofía Salido, Joaquín Altarejos, Manuel Nogueras, and Adolfo Sánchez. 2005. "3-Methyl-3-(6,6,6a-trimethyl-hexahydro-cyclopenta[b]furan-2-yl)-butan-2-one" Molbank 2005, no. 1: M393. https://doi.org/10.3390/M393

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