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Issue 11, 2013
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1,2,3-Trimethoxypropane, a glycerol-based solvent with low toxicity: new utilization for the reduction of nitrile, nitro, ester, and acid functional groups with TMDS and a metal catalyst

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Abstract

1,2,3-Trimethoxypropane (1,2,3-TMP) was prepared from glycerol in one step in good yield and selectivity by phase transfer catalysis. According to OECD guidelines, a toxicity study was realized for this compound. It revealed that 1,2,3-TMP has a low acute toxicity, no skin sensitization, no mutagenicity and no ecotoxicity in an aquatic environment. This compound was also used as a solvent for the reduction of organic functions using either aluminium hydride or 1,1,3,3-tetramethyldisiloxane (TMDS) as a benign hydride source. In particular, a new process for the reduction of nitriles to amines in 2-MeTHF and in 1,2,3-TMP was developed, using TMDS in combination with copper triflate (Cu(OTf)2).

Graphical abstract: 1,2,3-Trimethoxypropane, a glycerol-based solvent with low toxicity: new utilization for the reduction of nitrile, nitro, ester, and acid functional groups with TMDS and a metal catalyst

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Publication details

The article was received on 07 Jun 2013, accepted on 14 Aug 2013 and first published on 14 Aug 2013


Article type: Communication
DOI: 10.1039/C3GC41082J
Citation: Green Chem., 2013,15, 3020-3026
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    1,2,3-Trimethoxypropane, a glycerol-based solvent with low toxicity: new utilization for the reduction of nitrile, nitro, ester, and acid functional groups with TMDS and a metal catalyst

    M. Sutter, L. Pehlivan, R. Lafon, W. Dayoub, Y. Raoul, E. Métay and M. Lemaire, Green Chem., 2013, 15, 3020
    DOI: 10.1039/C3GC41082J

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