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Elena B. Usova
Ludmila I. Lysenko
Gennady D. Krapivin
Department of organic chemistry, Kuban State Technological University, Moskovskaya st. 2, Krasnodar, 350072, Russian Federation
Author to whom correspondence should be addressed.
Molecules 2000, 5(1), M127;
Submission received: 26 November 1999 / Accepted: 15 December 1999 / Published: 24 January 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 05 m127 i001
Furylcyclohexanones can be prepared by the reaction of acetoacetic ester (AAE) with b-furyl-a,b-unsaturated ketones [1,2]. To a mixture of a solution of sodium (0.5 g, 0.002 mol) in propanol (10 ml) and AAE (30 g, 0.23 mol) was added gradually with stirring furfurylidenacetone (13.6 g, 0.1 mol) over 15 min. During this time the mixture became homogeneous. It was left to stand at room temperature overnight before hexane (30 ml) and acetic acid (1 ml) were added. The white precipitate was filtered off, washed with hexane and recrystallized from ethanol to give 10.0g (40.3 %) of desired product as white crystals.
M.p. 114-115 °C (ethanol).
1H-NMR (60 MHz, CDCl3): 7.38 (d, J1=2.0 Hz, 1H, 5-H furan), 6.28 (dd, J1=2.0 Hz, J2=3.6 Hz, 1H, 4-H furan), 6.08 (d, J2=3.6 Hz, 1H, 3-H furan), 4.07 (q, J=7.0 Hz, 2H, CH3CH2O), 3.28-3.70 (m, 2H, 2-H, 3-Hcyclohexanone), 2.73 (broad s, 1H, OH), 1.92-2.50 (m, 4H, 4-H, 4-H, 6-H, 6-H cyclohexanone), 1.30 (s, 3H, CH3), 1.08 (t, J = 7.0 Hz, 3H, CH3CH2O).
IR (cm-1, nujol): 3420, 3150, 1725, 1695.
UV [lmax (nm), log e (dm3mol-1cm-1)] (ethanol): 217 (4.02).
Anal. calc. for C14H18O5 (266.28): C 63.14, H 6.81; found: C 63.52, H 6.52.

Supplementary Materials

The following supporting information can be downloaded at:


  1. Orlova, N.A.; Gerasimova, T.N.; Kudinova, M.A.; Tolmachev, N.A. Zhurnal Organicheskoy Khimii (Journal of Organic Chemistry, Russia. 1990, 20, 1313.
  2. Usova, E.B.; Lysenko, L.I.; Krapivin, G.D.; Kul’nevich, V.G. Khimiya Geterotsiklicheskikh Soedineniy (Chemistry of Heterocyclic Compounds, Russia) 1996, 5, 639.
Sample Availability: Available from the authors and from MDPI.

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MDPI and ACS Style

Usova, E.B.; Lysenko, L.I.; Krapivin, G.D. 2-Ethoxycarbonyl-3-(2-furyl)-5-hydroxy-5-methylcyclohexanone. Molecules 2000, 5, M127.

AMA Style

Usova EB, Lysenko LI, Krapivin GD. 2-Ethoxycarbonyl-3-(2-furyl)-5-hydroxy-5-methylcyclohexanone. Molecules. 2000; 5(1):M127.

Chicago/Turabian Style

Usova, Elena B., Ludmila I. Lysenko, and Gennady D. Krapivin. 2000. "2-Ethoxycarbonyl-3-(2-furyl)-5-hydroxy-5-methylcyclohexanone" Molecules 5, no. 1: M127.

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