90875-77-7Relevant articles and documents
An efficient method for the reductive conversion of acyclic esters to ethers via a TMS-protected acetal
Hart, Alison,Kelley, Sarah A.,Harless, Tyler,Hood, John A.,Tagert, Michael,Pigza, Julie A.
, p. 3024 - 3027 (2017)
We report an efficient two step process for the reduction of non-aromatic esters to the corresponding ethers via the intermediate TMS-protected acetal. The acetal formed after the first step can be carried on directly to the subsequent reduction to the ether without purification. The ester reduction step was monitored using in-situ ReactIR for disappearance of the C[dbnd]O peak, allowing for the exact determination of time and equivalents of the reducing agent. Furthermore, use of TMS-imidazole to form the acetal has allowed us to dramatically reduce the overall reaction time required for the two step procedure.
A Convenient One-Pot Method for the Hydroxymethylation of Grignard Reagents
Ogle, C. A.,Wilson, T. E.,Stowe, J. A.
, p. 495 - 496 (2007/10/02)
Grignard reagents and alkynyllithiums can be hydroxymethylated in a two-step one-pot reaction by reaction of a Grignard reagent with 1-chloro-2-(chloromethoxy)ethane (1), followed by treatment with sodium-potassium alloy and aqueous workup.The reaction was found to work for primary, secondary, tertiary, benzylic, allylic and aryl Grignard reagents in yields ranging from 57 - 95 percent.