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

Marc Sutter (1) , Leyla Pehlivan (1) , Romain Lafon (1) , Wissam Dayoub (1) , Yann Raoul (2) , Estelle Métay (1) , Marc Lemaire (3)

1 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
2 Sofiprotéol - 1, rue de Monceau, CS 60003, 75378 Paris Cedex 08, France
3 CASYEN - Catalyse Synthèse et Environnement

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).

Domaines: Chimie organique

Marc Sutter, Leyla Pehlivan, Romain Lafon, Wissam Dayoub, Yann Raoul, et al.. 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. Green Chemistry, 2013, 15, pp.3020-3026. ⟨hal-01179479⟩