Synlett 2010(19): 2861-2866  
DOI: 10.1055/s-0030-1259028
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Step Conversion of Alcohols into Thioesters

Hassan Zali Boeini*, Mehdi Mobin
Department of Chemistry, University of Isfahan, 81746-73441, Isfahan, Iran
Fax: +98(311)6689732; e-Mail: [email protected];
Further Information

Publication History

Received 18 September 2010
Publication Date:
03 November 2010 (online)

Abstract

A one-step conversion of alcohols into thioesters under solvent-free conditions is reported. The alcohols were reacted with primary thioamides in the presence of p-toluenesulfonic acid under solvent-free conditions to produce the corresponding thioesters in good to excellent yields.

    References and Notes

  • 1 Vallari DS. Jackowski S. Rock CO. J. Biol. Chem.  1987,  262:  2468 
  • 2 Stindl A. Keller U. J. Biol. Chem.  1993,  268:  10612 
  • 3 Dittmann J. Wenger RM. Kleinkauf H. Lawen A.
    J. Biol. Chem.  1994,  269:  2841 
  • 4 Stachelhaus T. Huser A. Marahiel MA. Chem. Biol.  1996,  3:  913 
  • 5 Kanda Y. Ashizawa T. Kakita S. Takahashi Y. Kono M. Yoshida M. Saitoh Y. Okabe M. J. Med. Chem.  1999,  42:  1330 
  • 6 Mroszczak E, and Runkel R. inventors; US Patent 4 397  862.  1983; Chem. Abstr. 1983, 99, 146134
  • 7 Venuti MC. Young GM. Maloney PG. Johnson D. McGreevy K. Pharm. Res.  1989,  6:  867 
  • 8 Greenlee ML. Laub JB. Balkovec JM. Hammond ML. Hammond GG. Pompliano DL. Epstein-Toney JH. Bioorg. Med. Chem. Lett.  1999,  9:  2549 
  • 9 Olsen J. Bjørnsdottir I. Tjørnelund J. Hansen SH.
    J. Pharm. Biomed. Anal.  2002,  29: 
  • 10 Matsumoto K. Costner EA. Nishimura I. Ueda M. Willson CG. Macromolecules  2008,  41:  5674 
  • 11 Kricheldorf HR. Schwarz G. J. Macromol. Sci., Part A: Pure Appl. Chem.  2007,  44:  625 
  • 12 Kameyama A. Kimura Y. Nishikubo T. Macromolecules  1997,  30:  6494 
  • 13 Yang W. Drueckhammer DG. J. Am. Chem. Soc.  2001,  123:  11004 
  • 14a Johnson JS. Evans DA. Acc. Chem. Res.  2000,  33:  325 
  • 14b Fortner KC. Shair MD. J. Am. Chem. Soc.  2007,  129:  1032 
  • 14c Gennari C. Vulpetti A. Pain G. Tetrahedron  1997,  53:  5909 
  • 14d Kobayashi S. Uchiro H. Fujishita Y. Shiina I. Mukaiyama T. J. Am. Chem. Soc.  1991,  113:  4247 
  • 15 Boeini ZH. Kashan EM. Green Chem.  2009,  11:  1987 
  • 16 Gopinath P. Vidyarini RS. Chandrasekaran S. J. Org. Chem.  2009,  74:  6291 
  • 17 Basu B. Paul S. Nanda AK. Green Chem.  2010,  5:  767 
  • 18 Krayushkin MM. Lichitskii BV. Mikhalev AP. Nabatov BV. Dudinov AA. Ivanov SN. Russ. J. Org. Chem.  2006,  42:  860 
  • 19a Jagodzinski ST. Chem. Rev.  2003,  103:  197 
  • 19b Moghaddam MF. Boeini ZH. Synlett  2005,  1612 
  • 20a Ralston AW. Vander Wal RJ. McCorkel MR.
    J. Org. Chem.  1939,  4:  68 
  • 20b Zbruyev OI. Stiasni N. Kappe CO. J. Comb. Chem.  2003,  5:  145 
  • 20c Charette AB. Grenon M. J. Org. Chem.  2003,  68:  5792 
  • 20d Olsson R. Hansen HC. Andersson CM. Tetrahedron Lett.  2000,  41:  7947 
  • 20e Polshettiwar V. Kaushik MP. Tetrahedron Lett.  2006,  47:  2315 
21

Complete experimental procedures and relevant ¹H and ¹³C NMR spectra and elemental microanalyses for new compounds are available in the Supporting Information

22

General Procedure: In a round-bottom flask, thioamide (1 mmol), alcohol (1.2 mmol), and p-TsOH (1 mmol) were heated to melt and heating was continued at 100 ˚C for 60 min. The reaction mixture was then poured into H2O (10 mL) with vigorous stirring. Thereafter an oily residue was left, which soon solidified to a semi-crystalline mass. The solid was filtered and washed with H2O (2 × 10 mL). Finally the solid compound was recrystallized from EtOH (95%) to afford pure thioesters as white or pale-yellow needles with a characteristic odor. Compound 3s: Mp 127-129 ˚C (EtOH); ¹H NMR (400 MHz, CDCl3): δ = 7.86 (d, J = 7.6 Hz, 2 H), 7.40 (d, J = 7.6 Hz, 2 H), 2.27 (m, 6 H), 2.11 (s, 3 H), 1.75-1.85 (m, 6 H); ¹³C NMR (100 MHz, CDCl3): δ = 191.3, 139.2, 136.7, 128.7, 128.3, 51.5, 41.9, 36.3, 29.9; Anal. Calcd for C17H19ClOS: C, 66.54; H, 6.24; S, 10.45. Found: C, 66.75; H, 6.09; S, 10.59