Tetrahydrofuran → 2-Hydroxyethyl Methacrylate

Participants

Reaction Steps

The 1H NMR spectrum of the PIB before, as seen in FIG. 7a, and after, as seen in FIG. 7b, methacrylation are provided. The resonance at δ3.6 ppm, corresponding to the —CH2— protons next to the hydroxyl group, as seen in FIG. 7a, disappeared and new resonances attributed to the vinylidene [δ5.6 (e2), δ6.1 (e1)], methyl [δ2.0 (f)] and methylene protons adjacent to the methacrylate end group [δ4.2 (g)] appeared at the expected positions. The integration ratios of (e2):(e1):(g):(f) were 1:1:2:3 which demonstrated quantitative functionalization. The use of THF solvent gave incomplete conversion after 24 hours, although PEG-MA was obtained in quantitative yield under similar conditions. At this point we do not understand the reason for this discrepancy. We hope to get a better understanding of the mechanism of enzymatic polymerizations, which we are actively investigating.

Provenance & Evidence