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DOI: 10.1055/s-0030-1259028
One-Step Conversion of Alcohols into Thioesters
Publication History
Publication Date:
03 November 2010 (online)
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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.
Key words
alcohols - carbocations - esters - sulfur - green chemistry
- Supporting Information for this article is available online:
- Supporting Information
- 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, andRunkel R. inventors; US Patent 4 397 862. ; 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: 7 - 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
References and Notes
Complete experimental procedures and relevant ¹H and ¹³C NMR spectra and elemental microanalyses for new compounds are available in the Supporting Information
22General 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