Chemoselective enrichment for compound isolation
AssigneeIndiana University Research and Technology Corporation
InventorsErin E. Carlson, Darci Trader
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Abstract
Chemoselective isolation of aliphatic hydroxyl group-containing and aromatic hydroxyl group-containing compounds is accomplished via formation of polymeric siloxyl ethers. Chemoselective release of aliphatic hydroxyl group-containing and aromatic hydroxyl group-containing compounds from polymeric siloxyl reagents is described.
Claims15
A process for preparing a second mixture selectively enriched in aromatic-hydroxyl group containing compounds from a first mixture comprising hydroxyl group containing compounds, where the hydroxyl group containing compounds include one or more functional groups selected from aromatic-hydroxyl groups and aliphatic-hydroxyl groups, the method comprising the steps of
- (a) contacting the first mixture with a polymeric reagent
- comprising a polymer having one or more functional groups of formula (CH2)n—O—Si(R1)(R2)X covalently attached to the polymer, wherein
- the functional group is capable of reacting with the hydroxyl group containing compounds when the first mixture containing the hydroxyl group containing compounds contacts the reagent;
- n is 1 to 4;
- R1 and R2 are independently in each instance C1-C8 alkyl or C3-C8 cycloalkyl;
- and
- X is selected from the group consisting of Cl, Br, and OS(O)2CF3;
- wherein one or more of the functional groups of the polymeric reagent forms a covalent bond with the hydroxyl group of one or more of the hydroxyl group containing compounds;
- (b) washing the polymer resulting from step (a) with a solvent selected from the group consisting of optionally branched C5-C10 alkanes, optionally branched C1-C5 alcohols, benzene, toluene, xylenes, C1-C5 alkyl C2-C5 alkanoates where each of the alkyl or the alkanoate is optionally branched, C1-C4 alkylnitriles, DMF, THF, dioxane, DMSO, C1-C4 haloalkanes, and combinations thereof;
- and
- (c) contacting the polymer resulting from step (b) with a mixture comprising 1,1,3,3-tetramethylguanidine (TMG) and R3CO2H, where R3 is C1-C8 alkyl to generate the second mixture.
A process for preparing a third mixture selectively enriched in aliphatic-hydroxyl group containing compounds from a first mixture comprising hydroxyl group containing compounds, where the hydroxyl group containing compounds include one or more functional groups selected from aromatic-hydroxyl groups and aliphatic-hydroxyl groups, the method comprising the steps
- (a) contacting the first mixture with a polymeric reagent
- comprising a polymer having one or more functional groups of formula (CH2)n—O—Si(R1)(R2)X covalently attached to the polymer, wherein
- the functional group is capable of reacting with hydroxyl group containing compounds when the mixture containing the compounds contacts the reagent;
- n is 1 to 4;
- R1 and R2 are independently selected in each instance from the group consisting of C1-C8 alkyl and C3-C8 cycloalkyl;
- and
- X is selected from the group consisting of Cl, Br, and OS(O)2CF3;
- wherein one or more of the functional groups forms a covalent bond with the hydroxyl group of one or more of the hydroxyl group containing compounds;
- (b) washing the polymer resulting from step (a) with a solvent selected from the group consisting of optionally branched C5-C10 alkanes, optionally-branched C1-C5 alcohols, benzene, toluene, xylenes, C1-C5 alkyl C2-C5 alkanoates, where each of the alkyl or the alkanoate is optionally branched, C1-C4 alkyl nitriles, DMF, THF, dioxane, DMSO, C1-C4 haloalkanes, and combinations thereof;
- (c) contacting the polymer resulting from step (b) with a mixture comprising 1,1,3,3-tetramethylguanidine (TMG) and R3CO2H, where R3 is C1-C8 alkyl to generate the second mixture;
- (d) washing the polymer resulting from step (c) with a solvent selected from the group consisting of optionally branched C5-C10 alkanes, optionally-branched C1-C5 alcohols, benzene, toluene, xylenes, C1-C5 alkyl C2-C5 alkanoates, where each of the alkyl or the alkanoate is optionally branched, C1-C4 alkylnitriles, DMF, THF, dioxane, DMSO, C1-C4 haloalkanes, and combinations thereof;
- and
- (e) contacting the polymer resulting from step (d) with a mixture of HF and pyridine.
Dependencies are inferred from the claim text.