A simple, rapid and efficient protocol for the synthesis of methylthiomethyl esters under Swern oxidation conditions

被引：22
|
作者：
Jadhav, Sunil B. [1 ]
Ghosh, Usha [1 ]
机构：
[1] Nicholas Piramal Res Ctr, Dept Med Chem, Bombay 400063, Maharashtra, India
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 14期
关键词：
Swern oxidation; carboxylic acids; methylthiomethyl esters;
D O I：
10.1016/j.tetlet.2007.02.036
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A rapid, mild and high yielding method for the synthesis of methylthiomethyl esters is reported from the corresponding aliphatic, aromatic and unsaturated carboxylic acids under Swern oxidation conditions using dimethylsulfoxide, oxalyl chloride and triethylamine at low temperature. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2485 / 2487
页数：3
相关论文
共 50 条
  • [1] Synthesis of Nitriles from Primary Amides or Aldoximes under Conditions of a Catalytic Swern Oxidation
    Ding, Rui
    Liu, Yongguo
    Han, Mengru
    Jiao, Wenyi
    Li, Jiaqi
    Tian, Hongyu
    Sun, Baoguo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (20): : 12939 - 12944
  • [2] One-pot synthesis of highly functionalized oxindoles under Swern oxidation conditions
    Lopez-Alvarado, Pilar
    Steinhoff, Judith
    Miranda, Sonia
    Avendano, Carmen
    Menendez, J. Carlos
    [J]. SYNLETT, 2007, (18) : 2792 - 2796
  • [3] Conversion of hydrazones to alkyl chlorides under Swern oxidation conditions
    Brewer, Matthias
    [J]. TETRAHEDRON LETTERS, 2006, 47 (44) : 7731 - 7733
  • [4] Preparation of nitriles from primary amides under swern oxidation conditions
    Nakajima, N
    Ubukata, M
    [J]. TETRAHEDRON LETTERS, 1997, 38 (12) : 2099 - 2102
  • [5] Oxidation of carbamate-protected alkylhydrazines to the corresponding hydrazones under Swern conditions
    Dupont, J
    Bemish, RJ
    McCarthy, KE
    Payne, ER
    Pollard, EB
    Ripin, DHB
    Vanderplas, BC
    Watrous, RM
    [J]. TETRAHEDRON LETTERS, 2001, 42 (08) : 1453 - 1454
  • [6] HBF4/ACN: A simple and efficient protocol for the synthesis of pyrazoles under ambient reaction conditions
    Hazarika, Roktopol
    Konwar, Manashjyoti
    Damarla, Krishnaiah
    Kumar, Arvind
    Sarma, Diganta
    [J]. SYNTHETIC COMMUNICATIONS, 2020, 50 (03) : 329 - 337
  • [7] A simple and efficient synthesis protocol for sulfonation of nitrobenzene under solvent-free conditions via a microreactor
    Chen, Yizheng
    Su, Yuanhai
    Jiao, Fengjun
    Chen, Guangwen
    [J]. RSC ADVANCES, 2012, 2 (13) : 5637 - 5644
  • [8] A SIMPLE AND EFFICIENT SYNTHESIS OF CHLOROTETROLIC ESTERS
    OLOMUCKI, M
    LEGALL, JY
    BARRAND, I
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (22) : 1290 - 1291
  • [9] Tandem oxidation/halogenation of aryl allylic alcohols under Moffatt-Swern conditions
    Yin, Jiandong
    Gallis, Christina E.
    Chisholm, John D.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (18): : 7054 - 7057
  • [10] RAPID AND EFFICIENT SYNTHESIS OF (R)-ARYLOXYPROPIONIC ACID ESTERS UNDER MICROWAVE IRRADIATION
    Ochal, Zbigniew
    Durka, Krzysztof
    Banach, Lukasz
    [J]. SYNTHETIC COMMUNICATIONS, 2010, 40 (21) : 3209 - 3213
12345