2-(2/-Cinnamyl-1/,3/-oxazolyl)-1,3-dithiolane : To a mixture of 2-cinnamyl-1,3-oxazole-4-carboxaldehyde (2

Molecules 2001, 6, M270

2-(2'-Cinnamyl-1',3'-oxazolyl)-1,3-dithiolane

Fahim Ahmed

Department of Chemistry, Marquette University, P O Box 1881, Milwaukee, WI 53201-1881, USA
E-mail: [email protected]

Received: 27 October 2001 / Accepted: 15 December 2001 / Published: 20 December 2001

To a mixture of 2-cinnamyl-1,3-oxazole-4-carboxaldehyde [1,2] (2.8 g, 14 mmol) and ethanedithiol (2.3 g, 21 mmol) in methylene chloride (100 ml) was added boron trifluoride etherate (2.8 g, 21 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was washed with aqueous sodium hydroxide (5%, 50 ml), and aqueous phase was extracted with ether. The combined organic layers were dried (MgSO₄), and concentrated. The residue was purified by column chromatography (SiO₂, 3:1 hexanes/ethyl acetate) to give 2-(2'-cinnamyl-1',3'-oxazolyl)-1,3-dithiolane as a light yellow solid (2.25 g, 66%).

M.p. 78-82 °C.

TLC (Hexane/EtOAc 5:1): R_f 0.21

¹H NMR (CDCl₃): 7.55 (d, J=16.3, 1H); 7.49-7.44 (m, 3H); 7.39-6.31 (m, 3H); 6.89 (d, J=16.3, 1H); 5.52 (s, 1H), 3.34 (m, 4H).

¹³C NMR (CDCl₃): 163.0, 144.7, 137.3, 136.0, 135.3, 129.9, 129.5, 127.8, 114.4, 47.5, 39.6.

IR (neat): n_max 3149, 2934, 2919, 1716, 962 cm^-1.

Anal.calc. for C₁₄H₁₃NOS₂.H₂O (293.39): C 57.31, H 5.15, N 4.77; found: C 57.15, H 4.77, N 4.36.

Acknowledgment: The Financial support of the National Institute of Health (GM-42641) and the Marquette University Graduate School is acknowledged. The author would like to thank Dr. William A. Donaldson (E-mail: [email protected]) for his encouragement.

Reference

1. Evans, D.A.; Fitch, D. M.; Smith, T. E.; Cee, V. J. Application of Complex Aldol Reactions to the total Synthesis of Phorboxazole B. J. Am. Chem. Soc. 2000, 122, 10033-10046.

2. Ahmed, F. 2-Cinnamyl-1,3-oxazole-4-carboxaldehyde p-Toluenesulfonyl Hydrazone. Molecules2001, 6, M269.