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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 15
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Original Articles

On the Methylation of Carboxyl Groups with Methanesulfonyl Chloride in Pyridine

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Pages 2575-2579 | Received 19 Nov 2002, Published online: 17 Aug 2006

References

  • Siddiqui , B.S. , Firdous , Begum and Sabira , Begum . 2001 . A new reagent for the methylation of carboxyl groups . Tetrahedron Lett. , 42 ( 51 ) : 9059 – 9060 .
  • Minor corrections have been made in Table 1 from the published version (Entries 4 and 5)
  • Nicolaou , K.C. , Baran , P.S. , Zhong , Y.L. , Choi , H.S. , Fong , K.C. , He , Y. and Yoon , W.H. 1999 . New synthetic technology for the synthesis of hindered α-diazoketones via acyl mesylates . Org. Lett. , 1 ( 6 ) : 883 – 886 .
  • Dunn , A.D. , Mils , M.J. and Henry , W. 1982 . A simple, one-pot conversion of carboxylic acids into nitriles . Org. Prep. Proced. Int. , 14 ( 6 ) : 396 – 399 . and references cited therein
  • Chandrasekaran , S. and Turner , J.V. 1982 . A mild and versatile method for carboxy group activation and esterification . Synth. Comm. , 12 ( 9 ) : 727 – 731 . and references cited therein
  • The molar ratios of pyridine given in the general procedure and in the case of ursolic acid (3) differ. The general procedure calls for 1 mmol of carboxylic acid dissolved in 1.2 mmol of pyridine, which is probably a misprint (this concentration is impossible to achieve). In the case of 3, the volume of pyridine (2 mL) does not correspond to the stated number of mmols (0.3 mmol) (See Ref. 1)
  • Hazen , G.G. and Rosenburg , D.W. 1964 . Preparation of 9(11)-unsaturated steroids. A novel reagent system . J. Org. Chem. , 29 ( 7 ) : 1930 – 1932 .
  • Under these conditions benzoic acid (1) gave an ˜1:1 mixture of methyl benzoate (2) and 1

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