Benzyl Alcohol → 6-(Benzyloxy)-2,3-dihydro-1H-inden-1-one

Participants

Reaction Steps

A solution of 6-hydroxyindan-1-one (1.60 g, 10.8 mmol (M. Phialas, P. G. Sammes, P. D. Kennewell, R. Westwood, J. Chem. Soc. Perkin Trans. 1: 687 (1984)), benzyl alcohol (1.23 mL, 11.9 mmol), triphenylphosphine (4.25 g, 16.2 mmol) under a N2 atmosphere in THF (100.0 mL) was treated with diethyl azodicarboxylate (2.55 mL, 16.2 mmol). The mixture was allowed to stir for 4 h then quenched with H2O. The mixture was then extracted with hexane (3×50 mL), the organic layers combined, dried with Na2SO4, and the solvent removed in vacuo. The residue was then submitted to column chromatography (SiO2 260-400 mesh, 4:1 hexanes: ethyl acetate) to provide the title compound (1.852 g, m.p. 99°-101° C.) as a solid. 'H NMR (400 MHz, CDCl3) δ 7.445-7.305 (m, 6H), 7.272-7.247 (m, 2H), 5.084 (s, 2H), 3.079 (m, 2H), 2.723-2.694 (m, 2H) .

Provenance & Evidence