The title compound, C13H13NO3, was synthesized by acetylation of ethyl 1H-indole-3-carboxylate. The aromatic ring system of the molecule is essentially planar, but the saturated ethyl group is also located within this plane and the overall r.m.s. deviation from planarity is only 0.034 Å. Pairs of C—H⋯O interactions connect molecules into chains along the diagonal of the unit cell. Molecules also form weakly connected dimers via π⋯π stacking interactions of the indole rings with centroid–centroid separations of 3.571 (1) Å. C—H⋯π interactions between methylene and methyl groups and the indole and benzene ring complete the directional intermolecular interactions found in the crystal structure.
An unusual reduction of the aryl-substituted 3-hydroxyacrylic acid ester 1 by BH 3 results in the propenoic acid ethyl ester 3. We were able to proVe the presence of an intermediate 2 containing a cyclic O-BH 2 r OdC< moiety in 2 by using 1 H-11 B and 1 H-13 C{ 11 B} NMR correlation experiments.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.