A Facile Preparation of Some Furylesters

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• All reactions were performed in open bottles protected from moisture by a CaCl2 tube. Reactions below 0°C were performed in a kryostate LAUDA KW 90. Infrared spectra were recorded on a Perkin-Elmer 257 Grating Infrared Spectrometer. H-NMR were recorded on a Perkin-Elmer R-12 instrument at 60 MHz in CDCL3 relative to TMS. Splitting patterns are designated as s (singlet), d (doublet), t (triplet), q (quartet) and m (multiplet); addition of br indicates a broadened pattern. Coupling constants are given in Hz. The splitting pattern in the furyl moiety are given as m for simplicity, the coupling constants are of the order 1, 2 and 3 Hz, however the pattern is not completely first order. Carbon nuclear magnetic resonans (13C NMR) spectra were determined on the Jeol FX-60 instrument at 15.03 MHz; chemical shifts in the proton noise decoupled spectra are reported in ppm downfield from TMS. The splitting pattern (multiplicity) in the proton coupled spectra are given as s (singlet), d (doublet), t (triplet) and q (quartet) for none, one, two and three protons respectively one bond coupled to the carbon atom reported. Mass spectra were recorded by Mr. M. Reunanen on a VG Micromass 7070 E instrument or on a LKB 9000 instrument both working at an ionizing voltage of 70 eV. Melting points were determined on a Gallenkamp apparatus in open capillary tubes and are uncorrected. Boiling points are uncorrected. Microanalyses were performed by Micro Kemi AB, Uppsala, Sweden; The % nitrogen is not within 0.4%, which however according to the performer is normal for the method when oils are analysed. Residues of triethylamine or derivatives thereof were not detected in substances reported pure. The specific rotation of 2c and was obtained from Huhtamäki OY, Leiras Chemicals. 2(5H)-furanone was prepared by the method of ours from furfural (JN, Pensar G., Synthesis in press) or by the procedure of Price and Judge (Org. Synth. 45, 22). Menthyl chloroformate was prepared from phosgene (20% solution in toluene 1.3 eq.) and (−)-menthol at 40°C overnight and was used directly after evaporation of toluene; other noncommercial chloroformates were prepared by essentially the same method. All other reagents were commercial. Acetonitrile was distilled from P2O5 unless freshly opened botlles were used. Triethylamine was distilled from and stored over KOH-pellets. Ether was dried over sodium
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• 1972 . Wiley . The multiplicity of peaks at δ = 16.4 − 34.0 in the 13C-NMR spectrum of 2c were assigned by comparing our spectrum with at known spectrum of (−)-menthol, spectrum 410 in Johnson & Jankowski; Carbo-13 NMR Spectra
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• Pure compounds are stable and clear for months without any precautions like excluding air fom their bottles. If the compounds however contain traces of hydrochloride salts they become brown in a few days
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