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Direct arylations on water: synthesis of 2,5-disubstituted oxazoles balsoxin and texaline

Royal Society of Chemistry
Publication Date
  • Chemistry


Microsoft Word - MFG_ESI_oxazoles.doc S1 Direct Arylations On Water: Synthesis of 2,5-Disubstituted Oxazoles Balsoxin and Texaline Stephan A. Ohnmacht,† Patrizia Mamone,† Andrew J. Culshaw‡ and Michael F. Greaney*† †University of Edinburgh, School of Chemistry, Joseph Black Building, King’s Buildings, West Mains Rd, Edinburgh EH9 3JJ, UK . ‡Global Discovery Chemistry, Novartis Horsham Research Centre, Wimblehurst Road, Horsham, West Sussex RH12 5AB, UK Part A: Experimental Procedures General NMR spectra were obtained from a Brüker AC250 (250MHz) instrument and calibrated to residual solvent peaks: 1H - CDCl3, 7.26 ppm and 13C – CDCl3, 77.0 ppm. The 1H-NMR data is presented as follows: chemical shift (in ppm on the δ scale), integration, multiplicity (s= singlet, d= doublet, t= triplet, q= quartet, m= multiplet), coupling constant (J in Hz) and structural assignment. The 13C-NMR data is reported as ppm on the δ scale, followed by the structural assignment. High resolution mass spectrometry was performed by the EPSRC National Mass Spectrometry Service Centre, Swansea, using Finnigan MAT 95XP and Finnigan MAT 900XLT instruments ES analysis. The data is presented as the ionisation method, followed by the calculated and measured masses. TLC was preformed on Merck 60 F254 silica plates and visualised by UV light and/or KMnO4 stain. Compound purification was carried out by wet flash column chromatography using Merck Kieselgel 60 (particle size 35-70). Eluent constitution is quoted as ratios or percentages. All solvents were dried before use unless otherwise stated. Anhydrous solvents were obtained from a solvent purification system supplied by or a PureSolv solvent purification system supplied by Innovative Technologies Inc. All other chemicals were purchased from a chemical supplier and used as received. Supplementary Material (ESI) for Chemical Communications This jou

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