m0127

Molecules 2000, 5, M127

2-Ethoxycarbonyl-3-(2-furyl)-5-hydroxy-5-methylcyclohexanone

Elena B. Usova, Ludmila I. Lysenko and Gennady D. Krapivin

Department of organic chemistry, Kuban State Technological University, Moskovskaya st. 2, Krasnodar, 350072, Russian Federation. Phone +7 8612 559556, E-mail: [email protected]

Received: 26 November 1999 / Accepted: 15 December 1999 / Published: 24 January 2000

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-H cyclohexanone), 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 [l_max(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.

References

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.

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.